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EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes

phthalide
3H-2-benzofuran-1-one

Supplier Sponsors

BOC Sciences

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GSC127473104108 GSC127473104108
Product(s):
87-41-2 Phthalide

Penta International

Penta International Corporation

Chemistry innovation
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For over 30 years, Penta Manufacturing Company has played a growing role in worldwide chemistry innovations and applications. As an industry leader, Penta continues to pioneer chemistry-based solutions for practically every area of commerce. Our products and expertise have helped fuel technical advances in dozens of commercial applications including flavoring, coloring, fragrances and chemical processes.
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GSC127473104108 GSC127473104108
Product(s):
16-48750 PHTHALIDE

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GSC127473104108 GSC127473104108
Product(s):
P0401 Phthalide >98.0%(T)
SDS

Name:	3H-2-benzofuran-1-one
CAS Number:	87-41-2	3D/inchi
ECHA EINECS - REACH Pre-Reg:	201-744-0
FDA UNII:	8VV922U86J
Nikkaji Web:	J95.650C
Beilstein Number:	0114632
MDL:	MFCD00005906
XlogP3:	0.80 (est)
Molecular Weight:	134.13422000
Formula:	C8 H6 O2
BioActivity Summary:	listing
NMR Predictor:	Predict (works with chrome, Edge or firefox)

Category:flavor and fragrance agents

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:	Search
Google Books:	Search
Google Scholar: with word "volatile"	Search
Google Scholar: with word "flavor"	Search
Google Scholar: with word "odor"	Search
Perfumer and Flavorist:	Search
Google Patents:	Search
US Patents:	Search
EU Patents:	Search
Pubchem Patents:	Search
PubMed:	Search
NCBI:	Search
DG SANTE Food Flavourings:	10.056 phthalide
FEMA Number:	4195 phthalide
FDA:	No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):	87-41-2 ; PHTHALIDE

Physical Properties:

Appearance:	white powder (est)
Assay:	98.00 to 100.00
Food Chemicals Codex Listed:	No
Melting Point:	75.00 to 76.00 °C. @ 760.00 mm Hg
Boiling Point:	290.00 to 291.00 °C. @ 760.00 mm Hg
Boiling Point:	144.00 to 145.00 °C. @ 10.00 mm Hg
Vapor Pressure:	0.002000 mmHg @ 25.00 °C. (est)
Flash Point:	> 300.00 °F. TCC ( > 148.89 °C. )
logP (o/w):	0.800
Soluble in:
	alcohol
	propylene glycol @ 1%
	water, 1.836e+004 mg/L @ 25 °C (est)
Insoluble in:
	water

Organoleptic Properties:

Odor Type: coumarinic

Odor Strength:low

Substantivity:28 hour(s) at 1.00 % in propylene glycol

sweet tonka coumarinic powdery coconut phenolic lactonic

Odor Description:at 100.00 %. sweet tonka coumarin powdery coconut phenolic lactonic
Luebke, William tgsc, (2006)

Odor sample from: Sigma-Aldrich

Flavor Type: coumarinic

sweet coumarinic coconut creamy anisic green vegetable floral

Taste Description: at 100.00 ppm in water. sweet coumarin coconut creamy anisic green vegetable floral
Luebke, William tgsc, (2006)

Odor and/or flavor descriptions from others (if found).

Cosmetic Information:

None found

Suppliers:

For experimental / research use only.

For experimental / research use only.

Penta International

Santa Cruz Biotechnology

For experimental / research use only.

For experimental / research use only.

Phthalide analytical standard

For experimental / research use only.

Phthalide >98.0%(T)

Safety Information:

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36 - Irritating to eyes. S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36 - Wear suitable protective clothing.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 5500 mg/kg (Moreno, 1979e) intraperitoneal-rat LD > 500 mg/kg National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 25, 1953.
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for phthalide usage levels up to:
	1.0000 % in the fragrance concentrate.

Maximised Survey-derived Daily Intakes (MSDI-EU):		0.80 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI):		3900 (μg/person/day)
Threshold of Concern:		90 (μg/person/day)
Structure Class:		III
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 22
Click here to view publication 22
		average usual ppm	average maximum ppm
baked goods:		5.00000	25.00000
beverages(nonalcoholic):		-	-
beverages(alcoholic):		-	-
breakfast cereal:		2.00000	10.00000
cheese:		3.00000	15.00000
chewing gum:		-	-
condiments / relishes:		2.00000	10.00000
confectionery froastings:		4.00000	20.00000
egg products:		-	-
fats / oils:		2.00000	10.00000
fish products:		1.00000	5.00000
frozen dairy:		3.00000	15.00000
fruit ices:		3.00000	15.00000
gelatins / puddings:		-	-
granulated sugar:		-	-
gravies:		-	-
hard candy:		-	-
imitation dairy:		3.00000	15.00000
instant coffee / tea:		-	-
jams / jellies:		-	-
meat products:		1.00000	5.00000
milk products:		3.00000	15.00000
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		2.00000	10.00000
processed vegetables:		-	-
reconstituted vegetables:		-	-
seasonings / flavors:		2.00000	10.00000
snack foods:		5.00000	25.00000
soft candy:		-	-
soups:		2.00000	10.00000
sugar substitutes:		-	-
sweet sauces:		2.00000	10.00000

Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
		average usage mg/kg	maximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0):		7.00000	35.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0):		5.00000	25.00000
Edible ices, including sherbet and sorbet (03.0):		10.00000	50.00000
Processed fruit (04.1):		7.00000	35.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2):		-	-
Confectionery (05.0):		10.00000	50.00000
Chewing gum (05.3):		-	-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0):		5.00000	25.00000
Bakery wares (07.0):		10.00000	50.00000
Meat and meat products, including poultry and game (08.0):		2.00000	10.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0):		2.00000	10.00000
Eggs and egg products (10.0):		-	-
Sweeteners, including honey (11.0):		-	-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0):		5.00000	25.00000
Foodstuffs intended for particular nutritional uses (13.0):		10.00000	50.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1):		5.00000	25.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2):		10.00000	50.00000
Ready-to-eat savouries (15.0):		20.00000	100.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0):		5.00000	25.00000

Safety References:

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 27 (FGE.27): One aromatic lactone from chemical group 11[1] - Scientific Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 80 (FGE.80) - Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008)
View page or View pdf

Flavouring Group Evaluation 80, Revision 1 (FGE.80Rev1): Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008)
View page or View pdf

EPI System: View

Chemical Carcinogenesis Research Information System:Search

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):87-41-2

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :6885

National Institute of Allergy and Infectious Diseases:Data

3H-2-benzofuran-1-one

Chemidplus:0000087412

RTECS:TI3520000 for cas# 87-41-2

References:

	3H-2-benzofuran-1-one
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	87-41-2
Pubchem (cid):	6885
Pubchem (sid):	134971567

Other Information:

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):	View
CHEBI:	View
CHEMBL:	View
KEGG (GenomeNet):	C09921
HMDB (The Human Metabolome Database):	HMDB32469
FooDB:	FDB010076
Export Tariff Code:	2932.29.4500
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
EFSA Update of results on the monitoring of furan levels in food:	Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:	Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:	Read Report

Potential Blenders and core components note

For Odor

No odor group found for these

7-

methyl coumarin replacer
FR

alliaceous

alliaceous

dibutyl sulfide
FL/FR

dipropyl disulfide
FL/FR

animal

6-

methyl quinoline
FL/FR

caramellic

2-iso

butyl-3-methyl pyrazine
FL/FR

chocolate

2,4,5-

trimethyl thiazole
FL/FR

citrus

methyl heptenone
FL/FR

coconut

alpha-

angelica lactone
FL/FR

coconut decanone methyl
FR

coconut naphthalenone
FL/FR

delta-

decalactone
FL/FR

delta-2-

dodecenolactone
FL/FR

gamma-

heptalactone
FL/FR

delta-

heptalactone
FL/FR

hexahydrocoumarin
CS

gamma-

octalactone
FL/FR

coumarinic

deertongue oil
FR

tonka ketone
FR

creamy

delta-

tridecalactone
FL/FR

para-

vanillyl alcohol
FL/FR

waxy lactone
FL/FR

ethereal

2-

methyl valeraldehyde
FL/FR

floral

clover fragrance
FR

linden flower absolute
FR

linden flower absolute replacer
FR

(Z)-

rose oxide
FL/FR

fruity

para-

anisyl methyl ketone
FL/FR

2-

benzofuran carboxaldehyde
FL/FR

methyl (Z)-5-octenoate
FL/FR

tolualdehydes (mixed o,m,p)
FL/FR

gamma-

undecalactone (aldehyde C-14 (so-called))
FL/FR

green

acetaldehyde butyl phenethyl acetal
FL/FR

iso

butyl methyl ketone
FL/FR

2-iso

butyl thiazole
FL/FR

cortex pyridine
FL/FR

galbanum decatriene
FL/FR

geranium thiazole
FL/FR

3-

hepten-2-one
FL/FR

(Z)-2-

hexen-1-ol
FL/FR

(Z)-3-

hexen-1-yl tiglate
FL/FR

(Z)-

leaf acetal
FL/FR

methyl heptine carbonate
FL/FR

narcissus flower absolute
FR

nerol oxide
FL/FR

(Z,Z)-3,6-

nonadien-1-ol
FL/FR

1-

penten-3-ol
FL/FR

herbal

3-

butylidene phthalide
FL/FR

2-

pentyl acetate
FL/FR

gamma-

valerolactone
FL/FR

mossy

musk

iso

ambrettolide
FL/FR

musty

cocoa butenal
FL/FR

spicy

saffron oil CO2 extract
FL/FR

sulfurous

3-(

methyl thio) hexanol
FL/FR

tobacco

deertongue absolute replacer
FR

tonka

6-

amyl-alpha-pyrone
FL/FR

deertongue absolute
FR

deertongue concrete
FR

deertongue oleoresin
FR

dihydrocoumarin replacer
FR

(±)-

dihydromint lactone
FL/FR

flouve absolute
FR

melilot absolute
FR

7-

methyl coumarin
CS

mint lactone
FL/FR

whiskey lactone
FL/FR

tropical

glyceryl 5-hydroxydecanoate
FL/FR

vanilla

propenyl guaethol
FL/FR

woody

alpha-

farnesene
FL/FR

alpha-

farnesene isomer
FL/FR

yeasty

2-

octen-4-one
FL/FR

For Flavor

No flavor group found for these

coconut naphthalenone
FL/FR

delta-2-

dodecenolactone
FL/FR

melilot oleoresin
FL

7-

methoxycoumarin
FL

(R)-

tonka furanone
FL

alliaceous

alliaceous

allyl thiopropionate
FL

dipropyl disulfide
FL/FR

animal

6-

methyl quinoline
FL/FR

celery

3-

butylidene phthalide
FL/FR

coconut

delta-

decalactone
FL/FR

massoia bark oil CO2 extract
FL

(R)-

massoia lactone
FL

coumarinic

coumarin flavor
FL

creamy

6-

amyl-alpha-pyrone
FL/FR

alpha-

angelica lactone
FL/FR

5,5-

dibutyl dihydrofuran-2(3H)-one
FL

dihydrocoumarin
FL

glyceryl 5-hydroxydecanoate
FL/FR

3-

hepten-2-one
FL/FR

massoia lactone
FL

mint lactone
FL/FR

delta-

tridecalactone
FL/FR

gamma-

undecalactone (aldehyde C-14 (so-called))
FL/FR

para-

vanillyl alcohol
FL/FR

waxy lactone
FL/FR

dairy

methyl (Z)-5-octenoate
FL/FR

2-

pentyl acetate
FL/FR

fruity

banana coconut cream flavor
FL

2,4-

hexadien-1-ol
FL

tolualdehydes (mixed o,m,p)
FL/FR

green

acetaldehyde butyl phenethyl acetal
FL/FR

iso

butyl methyl ketone
FL/FR

2-iso

butyl thiazole
FL/FR

2-iso

butyl-3-methyl pyrazine
FL/FR

cocoa butenal
FL/FR

cortex pyridine
FL/FR

cynara scolymus leaf extract
FL

dibutyl sulfide
FL/FR

dihydroxyacetophenone (mixed isomers)
FL

alpha-

farnesene
FL/FR

alpha-

farnesene isomer
FL/FR

galbanum decatriene
FL/FR

geranium thiazole
FL/FR

(Z)-2-

hexen-1-ol
FL/FR

(Z)-3-

hexen-1-yl tiglate
FL/FR

2-

hexyl pyridine
FL

horseradish oil
FL

(Z)-

leaf acetal
FL/FR

methyl heptenone
FL/FR

methyl heptine carbonate
FL/FR

4-

methyl thiazole
FL

nerol oxide
FL/FR

4-

penten-1-yl acetate
FL

1-

penten-3-ol
FL/FR

(Z)-

rose oxide
FL/FR

herbal

clover herb distillate (melilotus officinalis)
FL

lactonic

(±)-

dihydromint lactone
FL/FR

delta-

heptalactone
FL/FR

gamma-

heptalactone
FL/FR

gamma-

octalactone
FL/FR

metallic

3-(

methyl thio) hexanol
FL/FR

musk

iso

ambrettolide
FL/FR

nutty

2-

benzofuran carboxaldehyde
FL/FR

2,4,5-

trimethyl thiazole
FL/FR

radish

horseradish flavor
FL

spicy

para-

anisyl methyl ketone
FL/FR

saffron oil CO2 extract
FL/FR

sulfurous

broccoli flavor
FL

tonka

gamma-

valerolactone
FL/FR

vanilla

propenyl guaethol
FL/FR

vegetable

2-

methyl valeraldehyde
FL/FR

2-

octen-4-one
FL/FR

waxy

(Z,Z)-3,6-

nonadien-1-ol
FL/FR

woody

whiskey lactone
FL/FR

Potential Uses:

FR	amber
FR	chypre
FR	coconut
FR	moss
FR	tonka bean
FR	woody

Occurrence (nature, food, other):note

	tomato Search Trop Picture
	wine - up to 0.07 mg/kg Search Picture

Synonyms:

3H-2-	benzofuran-1-one
2-	benzofuran-1(3H)-one
	benzofuran-2(5H)-one
1-iso	benzofuranone
1(3H)-iso	benzofuranone
1-	phthalanone
	phthalolactone

Articles:

PubMed:Selenium-Catalyzed C(sp(3) )H Acyloxylation: Application in the Expedient Synthesis of Isobenzofuranones.

PubMed:N-butylidenephthalide Attenuates Alzheimer's Disease-Like Cytopathy in Down Syndrome Induced Pluripotent Stem Cell-Derived Neurons.

PubMed:Coupling of carboxylic acids with internal alkynes by supported ruthenium catalysts: direct and selective syntheses of multi-substituted phthalide derivatives.

PubMed:Addition-elimination versus Tishchenko reaction in the gas phase.

PubMed:One new ergostane-type steroid and three new phthalide derivatives from cultures of the basidiomycete Albatrellus confluens.

PubMed:The photoformation of a phthalide: a ketene intermediate traced by FSRS.

PubMed:Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins.

PubMed:Ru-catalyzed decarboxylative cyclization of mandelic acids with acrylates: facile access to the phthalide skeleton.

PubMed:Simultaneous Determination of 10 Components in Bu-Zhong-Yi-Qi Wan by Solid Phase Extraction-High Performance Liquid Chromatography with Diode Array Detection and Evaporative Light Scattering Detection.

PubMed:Comparative analysis of main aromatic acids and phthalides in Angelicae Sinensis Radix, Chuanxiong Rhizoma, and Fo-Shou-San by a validated UHPLC-TQ-MS/MS.

PubMed:Diastereomeric aziridine carbinol catalyzed enantioselective arylation reaction: toward the asymmetric synthesis of both enantiomers of chiral 3-aryl phthalide.

PubMed:Volatile compounds from roots, stems and leaves of Angelica acutiloba growing in Taiwan.

PubMed:Divergent synthesis of bioactive resorcinols isolated from the fruiting bodies of Hericium erinaceum: total syntheses of hericenones A, B, and I, hericenols B-D, and erinacerins A and B.

PubMed:New dimeric phthalides from Ligusticum sinense Oliv cv. Chaxiong.

PubMed:[Network pharmacology study on major active compounds of siwu decoction analogous formulae for treating primary dysmenorrhea of gynecology blood stasis syndrome].

PubMed:[A new phthalide from angelicae sinensis radix].

PubMed:Determination of bicuculline in rat plasma by liquid chromatography mass spectrometry and its application in a pharmacokinetic study.

PubMed:NHC-catalyzed oxidative cyclization reaction for the synthesis of 3-substituted phthalides.

PubMed:Effect of different drying methods on the quality of Angelicae Sinensis Radix evaluated through simultaneously determining four types of major bioactive components by high performance liquid chromatography photodiode array detector and ultra-high performance liquid chromatography quadrupole time-of-flight mass spectrometry.

PubMed:Isolation and characterization of steroids, phthalide and essential oil of the fruits of Kelussia odoratissima Mozaff., an endemic mountain celery.

PubMed:Bioactive phthalides from Ligusticum sinense Oliv cv. Chaxiong.

PubMed:Two new phthalides with BuChE inhibitory activity from Ligusticum chuanxiong.

PubMed:One-pot synthesis of 3-alkylidenephthalides from benzoic acids by a rhodium-catalyzed ortho-C-H acylation process.

PubMed:Chemistry, technology, and nutraceutical functions of celery (Apium graveolens L.): an overview.

PubMed:Rhodium(III)-amine dual catalysis for the oxidative coupling of aldehydes by directed C-H activation: synthesis of phthalides.

PubMed:Quantum chemical and experimental studies on the structure and vibrational spectra of an alkaloid--Corlumine.

PubMed:Three new resorcylic acid derivatives from Sporotrichum laxum.

PubMed:DOPA and DHN pathway orchestrate melanin synthesis in Aspergillus species.

PubMed:3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.

PubMed:Structure elucidation of degradation products of Z-ligustilide by UPLC-QTOF-MS and NMR spectroscopy.

PubMed:A phthalide derivative isolated from endophytic fungi Pestalotiopsis photiniae induces G1 cell cycle arrest and apoptosis in human HeLa cells.

PubMed:Targeted and untargeted phytochemistry of Ligusticum canbyi: indoleamines, phthalides, antioxidant potential, and use of metabolomics as a hypothesis-generating technique for compound discovery.

PubMed:Potential antitumor agent from the endophytic fungus Pestalotiopsis photiniae induces apoptosis via the mitochondrial pathway in HeLa cells.

PubMed:Photodissociation dynamics of fulvenallene, C7H6.

PubMed:Production of 5-hydroxy-7-methoxy-4-methylphthalide in a culture of Penicillium crustosum.

PubMed:Highly diastereoselective and enantioselective direct Michael addition of phthalide derivatives to nitroolefins.

PubMed:Online isolation and purification of four phthalide compounds from Chuanxiong rhizoma using high-speed counter-current chromatography coupled with semi-preparative liquid chromatography.

PubMed:Phthalide: a direct building-block towards P,O and P,N hemilabile ligands. Application in the palladium-catalysed Suzuki-Miyaura cross-coupling of aryl chlorides.

PubMed:Synthesis of complex benzenoids via the intermediate generation of o-benzynes through the hexadehydro-Diels-Alder reaction.

PubMed:Inhibition of monoamine oxidase by phthalide analogues.

PubMed:[Analysis on correlation between general efficacy and chemical constituents of danggui-chuanxiong herb pair based on artificial neural network].

PubMed:Unprecedented polyketides from a marine sponge-associated Stachylidium sp.

PubMed:Metabolism and pharmacokinetics of 3-n-butylphthalide (NBP) in humans: the role of cytochrome P450s and alcohol dehydrogenase in biotransformation.

PubMed:Palladium-catalyzed synthesis of isocoumarins and phthalides via tert-butyl isocyanide insertion.

PubMed:Identification of chemical constituents and larvicidal activity of Kelussia odoratissima Mozaffarian essential oil against two mosquito vectors Anopheles stephensi and Culex pipiens (Diptera: Culicidae).

PubMed:Total synthesis of 7',8'-dihydroaigialospirol.

PubMed:Design and synthesis of marine fungal phthalide derivatives as PPAR-γ agonists.

PubMed:Study on the absolute configurations of 3-alkylphthalides using TDDFT calculations of chiroptical properties.

PubMed:An indium-mediated allylative/transesterification DFT-directed approach to chiral C(3)-functionalized phthalides.

PubMed:Scientific basis of botanical medicine as alternative remedies for rheumatoid arthritis.

PubMed:Highly enantioselective regiodivergent allylic alkylations of MBH carbonates with phthalides.

PubMed:Enantiomeric derivatives of tokinolide B: absolute configuration and biological properties.

PubMed:Metabolic conversion from co-existing ingredient leading to significant systemic exposure of Z-butylidenephthalide, a minor ingredient in Chuanxiong Rhizoma in rats.

PubMed:Anti-inflammatory effects of (Z)-ligustilide through suppression of mitogen-activated protein kinases and nuclear factor-κB activation pathways.

PubMed:Noscapine induces mitochondria-mediated apoptosis in human colon cancer cells in vivo and in vitro.

PubMed:Phthalide and isocoumarin derivatives produced by an Acremonium sp. isolated from a mangrove Rhizophora apiculata.

PubMed:Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones.

PubMed:CN-assisted oxidative cyclization of cyano cinnamates and styrene derivatives: a facile entry to 3-substituted chiral phthalides.

PubMed:Direct asymmetric Mannich reaction of phthalides: facile access to chiral substituted isoquinolines and isoquinolinones.

PubMed:Simultaneous determination of nine related substances in p-phthalic acid residue by RP-HPLC.

PubMed:Copper(I) mediated facile synthesis of potent tubulin polymerization inhibitor, 9-amino-α-noscapine from natural α-noscapine.

PubMed:Highly stereoselective chemoenzymatic synthesis of the 3H-isobenzofuran skeleton. Access to enantiopure 3-methylphthalides.

PubMed:Stereoselective synthesis of hydroxy stilbenoids and styrenes by atom-efficient olefination with thiophthalides.

PubMed:Marilones A-C, phthalides from the sponge-derived fungus Stachylidium sp.

PubMed:An enantioselective approach toward 3,4-dihydroisocoumarin through the bromocyclization of styrene-type carboxylic acids.

PubMed:Two new compounds from an endophytic fungus Pestalotiopsis heterocornis.

PubMed:Ligusticum chuanxiong Hort: a review of chemistry and pharmacology.

PubMed:The atmospheric photolysis of o-tolualdehyde.

PubMed:Antagonistic properties of a natural product-Bicuculline with the gamma-aminobutyric acid receptor: studied through electrostatic potential mapping, electronic and vibrational spectra using ab initio and density functional theory.

PubMed:Two phthalide dimers from the radix of Angelica sinensis.

PubMed:Phthalide derivatives with antifungal activities against the plant pathogens isolated from the liquid culture of Pestalotiopsis photiniae.

PubMed:Ligustilide: a novel TRPA1 modulator.

PubMed:Synthesis of biarylketones and phthalides from organoboronic acids and aldehydes catalyzed by cobalt complexes.

PubMed:Phthalides and other constituents from Ligusticum porteri; sedative and spasmolytic activities of some natural products and derivatives.

PubMed:Ruthenium-catalyzed oxidative C-H bond alkenylations in water: expedient synthesis of annulated lactones.

PubMed:Adulticidal activity of phthalides identified in Cnidium officinale rhizome to B- and Q-biotypes of Bemisia tabaci.

PubMed:Phthalide-derived novel fluoroionophores incorporating picolylamino receptors: synthesis and response to metal cations.

PubMed:Identification of the major constituents in Xuebijing injection by HPLC-ESI-MS.

PubMed:Cytotoxic bibenzyls, and germacrane- and pinguisane-type sesquiterpenoids from Indonesian, Tahitian and Japanese liverworts.

PubMed:Benzannulation for the regiodefined synthesis of 2-alkyl/aryl-1-naphthols: total synthesis of arnottin I.

PubMed:Correlative analysis of metabolite profiling of Danggui Buxue Tang in rat biological fluids by rapid resolution LC-TOF/MS.

PubMed:Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.

PubMed:The actions of benzophenanthridine alkaloids, piperonyl butoxide and (S)-methoprene at the G-protein coupled cannabinoid CB₁ receptor in vitro.

PubMed:New isocourmarin and phthalide derivatives from the rhizomes of Matteuccia orientalis.

PubMed:Metabolic profiling of GuanXin II prescription based on metabolic fingerprinting and chemical analysis.

PubMed:L-3-n-butyl-phthalide alleviates hydrogen peroxide-induced apoptosis by PKC pathway in human neuroblastoma SK-N-SH cells.

PubMed:A practical total synthesis of (+)-spirolaxine methyl ether.

PubMed:Palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehyde to access 3-aryl- and alkenylphthalides.

PubMed:Chemical composition, antibacterial and antioxidant activity of the essential oil of Bupleurum longiradiatum.

PubMed:[Analysis of volatile oils of Ligusticum chuanxiong Hort. from different geographical origins by comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry].

PubMed:Novel phthalide compounds from Sparassis crispa (Hanabiratake), Hanabiratakelide A-C, exhibiting anti-cancer related activity.

PubMed:Synthesis of demethylated nidulol via an intramolecular Michael reaction.

PubMed:A new sesquiterpenoid from Ligusticum chuanxiong Hort.

PubMed:Rhodium-catalyzed cascade reaction: aryl addition/intramolecular esterification to access 3-aryl and 3-alkenyl phthalides.

PubMed:Transition metal-catalyzed addition reactions of arylboronic acids with alkyl 2-formylbenzoates: efficient access to chiral 3-substituted phthalides.

PubMed:Two new compounds from the roots of Ligusticum chuanxiong.

PubMed:Identification and comparative quantification of bio-active phthalides in essential oils from si-wu-tang, fo-shou-san, radix angelica and rhizoma chuanxiong.

PubMed:Synthesis of chiral 3-substituted phthalides by a sequential organocatalytic enantioselective aldol-lactonization reaction. Three-step synthesis of (S)-(-)-3-butylphthalide.

PubMed:Efficient synthesis of 3-arylphthalides using palladium-catalyzed arylation of aldehydes with organoboronic acids.

PubMed:Phthalides by rhodium-catalyzed ketone hydroacylation.

PubMed:Catalytic enantioselective synthesis of chiral phthalides by efficient reductive cyclization of 2-acylarylcarboxylates under aqueous transfer hydrogenation conditions.

PubMed:A novel compound from celery seed with a bactericidal effect against Helicobacter pylori.

PubMed:New antitumour fungal metabolites from Alternaria porri.

PubMed:Pesticide residues in coastal waters affected by rice paddy effluents temporarily stored in a wastewater reservoir in southern Japan.

PubMed:Identification of metabolites of Danggui Buxue Tang in rat urine by liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry.

PubMed:Biomimetic studies towards the cardinalins: synthesis of (+)-ventiloquinone L and an unusual dimerisation.

PubMed:Simultaneous determination of phenolic acids and phthalide compounds by liquid chromatography for quality assessment of Rhizoma cnidii.

PubMed:New phthalide glycosides from Helichrysum arenarium (L.) Moench.

PubMed:Daily variation of pesticides in surface water of a small river flowing through paddy field area.

PubMed:[Analysis of principal composition of ethyl acetate part in Huangqi Danggui decoction by HPLC-ESI-TOF-MS].

PubMed:2-(3-Oxo-1,3-dihydro-isobenzofuran-1-yl)-phthalazin-1(2H)-one.

PubMed:Bioactivity-guided fractionation and GC/MS fingerprinting of Angelica sinensis and Angelica archangelica root components for antifungal and mosquito deterrent activity.

PubMed:Photo-induced OH reactions of naphthalene and its oxidation products on SiO2.

PubMed:Inhibitory effects of noscapine on dopamine biosynthesis in PC12 cells.

PubMed:Enantioselective synthesis of the dimeric pyranonaphthoquinone core of the cardinalins using a late-stage homocoupling strategy.

PubMed:Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils.

PubMed:Dynamic nature of the ligustilide complex.

PubMed:Celery-based topical repellents as a potential natural alternative for personal protection against mosquitoes.

PubMed:Study of the anti-proliferative effects and synergy of phthalides from Angelica sinensis on colon cancer cells.

PubMed:Decrease of 4,5,6,7-tetrachlorophthalide in paddy field soil after aerial application.

PubMed:Rapid and sensitive screening and characterization of phenolic acids, phthalides, saponins and isoflavonoids in Danggui Buxue Tang by rapid resolution liquid chromatography/diode-array detection coupled with time-of-flight mass spectrometry.

PubMed:[GC-MS analysis of essential oil from rhizomes of Ligusticum chuanxiong cultivated in GAP base for Chinese medicinal materials of China].

PubMed:Variation of 4,5,6,7-tetrachlorophthalide in water after aerial application to rice cultivation area.

PubMed:Anti-Helicobacter pylori activity of derivatives of the phthalide-containing antibacterial agents spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015.

PubMed:Combinatorial anti-Trichophyton effects of Ligusticum chuanxiong essential oil components with antibiotics.

PubMed:Diketopiperazines and phthalides from a marine derived fungus of the order pleosporales.

PubMed:Flavor enhancement of chicken broth from boiled celery constituents.

PubMed:3',6'-Bis(diethyl-amino)-3H-spiro-[2-benzo-thio-phene-1,9'-xanthene]-3-thione.

PubMed:3-(2-Hydr-oxy-5-methyl-anilino)isobenzo-furan-1(3H)-one.

PubMed:3-(4-Methyl-piperazin-1-yl)isobenzofuran-1(3H)-one.

PubMed:3-(2,4-Dichloro-anilino)iso-benzo-furan-1(3H)-one.

PubMed:3-(2-Chloro-anilino)isobenzofuran-1(3H)-one.

PubMed:2-(3-Oxo-1,3-dihydro-isobenzofuran-1-ylamino)benzoic acid.

PubMed:Reductive dechlorination of chloroethenes by Dehalococcoides-containing cultures enriched from a polychlorinated-dioxin-contaminated microcosm.

PubMed:Synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether and the unnatural (2"S)-diastereomer.

PubMed:Postischemic administration of Z-Ligustilide ameliorates cognitive dysfunction and brain damage induced by permanent forebrain ischemia in rats.

PubMed:An alkyne strategy for the asymmetric synthesis of natural products: application to (+)-spirolaxine methyl ether.

PubMed:Synthesis and assignment of the absolute configuration of the anti-Helicobacter pylori agents CJ-12,954 and CJ-13,014.

PubMed:Chemical composition and antifungal activity of volatiles from three Opuntia species growing in Tunisia.

PubMed:Studies on antiproliferative effects of phthalides from Ligusticum chuanxiong in hepatic stellate cells.

PubMed:Direct access to 1,4-dihydroxyanthraquinones: the Hauser annulation reexamined with p-quinones.

PubMed:The structural diversity of phthalides from the Apiaceae.

PubMed:Comparative analysis of Ligusticum chuanxiong and related umbelliferous medicinal plants by high performance liquid chromatography-electrospray ionization mass spectrometry.

PubMed:Rhodium-catalyzed asymmetric one-pot transesterification and [2 + 2 + 2] cycloaddition leading to enantioenriched 3,3-disubstituted phthalides.

PubMed:Highly efficient cyclization of o-iodobenzoates with aldehydes catalyzed by cobalt bidentate phosphine complexes: a novel entry to chiral phthalides.

PubMed:Synthesis of the spiroacetal-containing anti-Helicobacter pylori agents CJ-12,954 and CJ-13,014.

PubMed:[High performance liquid chromatography-mass spectrometry analysis of radix Angelica sciensis].

PubMed:Absolute configuration of sporotricale and structure of 6-hydroxysporotricale.

PubMed:Concise synthesis of arnottin I and (-)-arnottin II.

PubMed:GABAergic phthalide dimers from Angelica sinensis (Oliv.) Diels.

PubMed:Runoff of aerially applied phthalide from paddy fields.

PubMed:Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding.

PubMed:Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst.

PubMed:Kinetics and products of photolysis and reaction with OH radicals of a series of aromatic carbonyl compounds.

PubMed:Identification of volatile components in Angelica species using supercritical-CO2 fluid extraction and solid phase microextraction coupled to gas chromatography-mass spectrometry.

PubMed:Synthesis of (+)-spirolaxine methyl ether.

PubMed:Uptake and UV-photooxidation of gas-phase PAHs on the surface of atmospheric water films. 1. Naphthalene.

PubMed:Two new phthalides from Ligusticum chuanxiong.

PubMed:Antiproliferative effect of Baylis-Hillman adducts and a new phthalide derivative on human tumor cell lines.

PubMed:Potent odorants characterize the aroma quality of leaves and stalks in raw and boiled celery.

PubMed:Determination of volatile flavor components in danggui cultivars by solvent free injection and hydrodistillation followed by gas chromatographic-mass spectrometric analysis.

PubMed:Total synthesis and biological evaluation of 22-hydroxyacuminatine.

PubMed:Photoinduced intramolecular charge transfer to meta position of benzene ring in 6-aminophthalides.

PubMed:Sulfated mesoporous alumina: a highly effective solid strong base catalyst for the Tishchenko reaction in supercritical carbon dioxide.

PubMed:Simultaneous qualitative and quantitative analyses of the major constituents in the rhizome of Ligusticum Chuanxiong using HPLC-DAD-MS.

PubMed:Synthesis of benz[d]indeno[1,2-b]pyran-5,11-diones: versatile intermediates for the design and synthesis of topoisomerase I inhibitors.

PubMed:[Protective effect of the pretreatment with Chuanxiong-phthalide A on the vascular endothelial cells impaired by the ischemia and reperfusion in isolated rats hearts].

PubMed:Efficient synthesis of isobenzofuran-1(3H)-ones (phthalides) and selected biological evaluations.

PubMed:A brief and convergent synthetic route to defucogilvocarcin M chromophore: the formal synthesis of WS-5995 A and C.

PubMed:Phthalide Lactones from Ligusticum chuanxiong inhibit lipopolysaccharide-induced TNF-alpha production and TNF-alpha-mediated NF-kappaB Activation.

PubMed:Two new zinniol-related phytotoxins from Alternaria solani.

PubMed:Larvicidal and adulticidal activity of alkylphthalide derivatives from rhizome of Cnidium officinale against Drosophila melanogaster.

PubMed:Anxiolytic effects of benzalphthalides.

PubMed:Novel antifungal compounds produced by Sterile Dark, an unidentified wheat rhizosphere fungus.

PubMed:[New dimeric phthalide derivative from Angelica sinensis].

PubMed:Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations.

PubMed:[Protective effect of ligusticum chuanxiong phthalides on focai cerebral ischemia in rats and its related mechanism of action].

PubMed:[Preparation of covalently bonded cellulose tris (4-methylbenzoate) derivative chiral stationary phases through a polymerization reaction].

PubMed:HPLC-coupled spectroscopic techniques (UV, MS, NMR) for the structure elucidation of phthalides in Ligusticum chuanxiong.

PubMed:The first enantioselective total synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether.

PubMed:A phthalide with in vitro growth inhibitory activity from an oidiodendron strain.

PubMed:Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster.

PubMed:Synthesis of phthalide derivatives using nickel-catalyzed cyclization of o-haloesters with aldehydes.

PubMed:Synthesis and absolute configuration of (-)-3-butyl-7-hydroxyphthalide, a cytotoxic metabolite of Penicillium vulpinum.

PubMed:Polar constituents of celery seed.

PubMed:Characterization of phthalides in Ligusticum chuanxiong by liquid chromatographic-atmospheric pressure chemical ionization-mass spectrometry.

PubMed:A new regiospecific preparation of xanthones.

PubMed:[Constituent analysis of essential oils from radix of Angelica acutiloba].

PubMed:Studies toward the total synthesis of mumbaistatin, a highly potent glucose-6-phosphate translocase inhibitor. Synthesis of a mumbaistatin analogue.

PubMed:Efficient heterogeneous catalytic intramolecular Tishchenko reaction of o-phthalaldehyde to phthalide with alkaline earth oxides.

PubMed:Application of microgels as polymer supports for organic synthesis: preparation of a small phthalide library, a scavenger, and a borohydride reagent.

PubMed:Role of spin trapping and P2Y receptor antagonism in the neuroprotective effects of 2,2'-pyridylisatogen tosylate and related compounds.

PubMed:Total synthesis of (+/-)-O-methyl PD 116740.

PubMed:New metabolites from sponge-derived fungi Curvularia lunata and Cladosporium herbarum.

PubMed:Sedanolide, a natural phthalide from celery seed oil: effect on hydrogen peroxide and tert-butyl hydroperoxide-induced toxicity in HepG2 and CaCo-2 human cell lines.

PubMed:A new alternative synthesis of 5-cyanophthalide, a versatile intermediate in the preparation of the antidepressant drug citalopram.

PubMed:Reactions of 3-(1-Hydroxyalkyl)phthalides with Acids: Synthesis of (Z)-3-Alkylidenephthalides and 3-Alkyl-8-hydroxyisocoumarins.

PubMed:[Chemical constituents of radix Angelicae Sinensis].

PubMed:Solid-phase directed ortho-lithiation and the preparation of a phthalide library.

PubMed:Structures of trihydroxynaphthalene reductase-fungicide complexes: implications for structure-based design and catalysis.

PubMed:Study of infrared and mass spectra of N-2-(3'-phthalide-yl)phthalazin-1-one.

PubMed:Synthesis of the proposed structure of fudecalone, an anticoccidial drimane terpenoid.

PubMed:Corollosporine, a new phthalide derivative from the marine fungus Corollospora maritima Werderm. 1069.

PubMed:Effects of methylenechloride-soluble fraction of Japanese angelica root extract, ligustilide and butylidenephthalide, on pentobarbital sleep in group-housed and socially isolated mice.

PubMed:CJ-12,954 and its congeners, new anti-Helicobacter pylori compounds produced by Phanerochaete velutina: fermentation, isolation, structural elucidation and biological activities.

PubMed:2-Acetylbenzoic acid: phthalide form.

PubMed:NTP Toxicology and Carcinogenesis Studies of Phenolphthalein (CAS No. 77-09-8) in F344/N Rats and B6C3F1 Mice (Feed Studies).

PubMed:Structure-activity relationships for inhibition of inosine monophosphate dehydrogenase by nuclear variants of mycophenolic acid.

PubMed:Metabolism of 6-chloro n-butyl phthalide in rat.

PubMed:A Concise, Enantioselective Synthesis of (-)- and (+)-Hongconin.

PubMed:[Investigation on in vivo metabolism of n-butyl phthalide].

PubMed:[Investigation on in vivo metabolism of 6-methoxy n-butyl phthalide].

PubMed:[HPLC determination of five constituents in plants of genus Ligusticum].

PubMed:[Studies on metabolism of 6-methoxy butyl phthalide by rat liver microsomes].

PubMed:[Studies on metabolism of 6-chloro butyl phthalide by rat liver microsomes].

PubMed:Competence effect of PDGF on Ki-67 antigen and DNA contents, and its inhibition by trichostatin-A and a butylydene phthalide BP-421 in primary smooth muscle cells of rat aorta by flow cytometry.

PubMed:Anti-competence effects of synthetic phthalide derivatives on platelet-derived growth factor-induced DNA synthesis in primary cultures of rat aorta smooth muscle cells.

PubMed:The structure-activity relationship between synthetic butylidenephthalide derivatives regarding the competence and progression of inhibition in primary cultures proliferation of mouse aorta smooth muscle cells.

PubMed:[Two phthalide dimers from rhizome of Ligusticum sinense Oliv cv. chaxiong].

PubMed:In vitro metabolism of aromatic nitriles.

PubMed:Phthalide-based host-plant resistance toSpodoptera exigua andTrichoplusia ni inApium graveolens.

PubMed:Solid-phase extraction and liquid chromatographic determination of monophthalates and phthalide extracted from solution administration sets.

PubMed:Chemoprevention of benzo[a]pyrene-induced forestomach cancer in mice by natural phthalides from celery seed oil.

PubMed:Mode of Action Studies on a Chiral Diphenyl Ether Peroxidizing Herbicide: Correlation between Differential Inhibition of Protoporphyrinogen IX Oxidase Activity and Induction of Tetrapyrrole Accumulation by the Enantiomers.

PubMed:Major antitermitic components of the heartwood of southern catalpa.

PubMed:(+)-Hydrastine, a potent competitive antagonist at mammalian GABAA receptors.

PubMed:Inhibitions of the GABA-induced currents of rat neurons by the alkaloid isocoryne from the plant Corydalis pseudoadunca.

PubMed:3-(3-Hydroxypropyl)-phthalide from Gentiana pedicellata.

PubMed:[Centrally acting muscle relaxant effect of phthalides (ligustilide, cnidilide and senkyunolide) obtained from Cnidium officinale Makino].

PubMed:[Metabolic products of microorganisms. 35. Asperdurin, a new antimycotic phthalide from Aspergillus duricaulis].

PubMed:[Facilitated performance of learning and memory in rats by 3-n-butyl phthalide].

PubMed:[The protective effect of 3-butyl phthalide on rat brain cells].

PubMed:Inhibitory mechanism of tritoqualine on histamine release from mast cells.

PubMed:[General pharmacological action of tritoqualine (TRQ; (+/-)-(R*)-7-amino-4, 5, 6-triethoxy-3-[(R*)-5, 6, 7, 8-tetrahydro-4-methoxy-6-methyl-1, 3-dioxolo [4, 5-g] isoquinolin-5-yl] phthalide].

PubMed:Phthalides in the essential oil from roots of Levisticum officinale.

PubMed:Effects of sodium picosulfate and other laxatives in cultured Chang cells.

PubMed:[Studies on the structure of a phthalide compound (author's transl)].

PubMed:[Effects of a new beta-blocking drug, DL 071-IT, on the myocardial contractile state in the waking dog; a comparison with 9 known beta blockaders].

PubMed:Labelled acetone and levulinic acid are formed when [14C]acetate is being converted to mycophenolic acid in Penicillium brevicompactum.

PubMed:Synthesis and pharmacological properties of a phthalide derivative containing methoxy groups.

PubMed:The structure of shihunine, a new phthalide-pyrrolidine alkaloid.

PubMed:Structure of catalpalactone, a new phthalide from Catalpa wood.

PubMed:[Phthalide as chief constituent of the essential oil of the fruit of Meum athamanticum Jacq].

PubMed:SHIHUNINE: A NEW PHTHALIDE-PYRROLIDINE ALKALOID.

PubMed:[Structure of the isomeric indones of the phthalide of beta-ethoxyphthalic anhydride].

Notes:

Used as a food additive [EAFUS]

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