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

apiole (parsley)
1,3-benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-

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Name:4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
CAS Number: 523-80-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-349-2
FDA UNII: QQ67504PXO
Nikkaji Web:J6.635D
Beilstein Number:0195747
XlogP3-AA:2.70 (est)
Molecular Weight:222.24038000
Formula:C12 H14 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:1787 apiole
 
Physical Properties:
Appearance:colorless to yellow green clear liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:1.12400 to 1.43500 @ 25.00 °C.
Pounds per Gallon - (est).: 9.353 to 11.941
Refractive Index:1.53600 to 1.53800 @ 20.00 °C.
Melting Point: 29.00 to 30.00 °C. @ 760.00 mm Hg
Boiling Point: 294.00 to 295.00 °C. @ 760.00 mm Hg
Boiling Point: 159.00 to 160.00 °C. @ 10.00 mm Hg
Vapor Pressure:0.003000 mmHg @ 25.00 °C. (est)
Flash Point: 243.00 °F. TCC ( 117.20 °C. ) (est)
logP (o/w): 3.481 (est)
Soluble in:
 alcohol
 acetone
 ether
 acetic acid
 water, 27.68 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: herbal
Odor Strength:low
parsley herbal
Odor Description:at 100.00 %. parsley faint
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
4,7-DIMETHOXY-5-(2-PROPANYL)-1,3-BENZODIOXOLE 95%
ExtraSynthese
For experimental / research use only.
Apiole (GC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Apioline
 
Safety Information:
 
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:
Not determined
Dermal Toxicity:
subcutaneous-frog LDLo 1515 mg/kg
PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 35, Pg. 342, 1895.

subcutaneous-mouse LDLo 1000 mg/kg
Bolletino della Societe Italiana di Biologia Sperimentale. Vol. 14, Pg. 291, 1939.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for apiole (parsley) usage levels up to:
 not for fragrance use.
 
Recommendation for apiole (parsley) flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):523-80-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10659
National Institute of Allergy and Infectious Diseases:Data
4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
Chemidplus:0000523808
RTECS:CY2500000 for cas# 523-80-8
 
References:
 4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10659
Pubchem (sid):134977796
 
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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10429
HMDB (The Human Metabolome Database):HMDB33776
FooDB:FDB011929
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
For Odor
amber
angelica root oil
FL/FR
animal
iso
butyl quinoline
FR
anisic
estragole
FL/FR
balsamic
cinnamyl formate
FL/FR
camphoreous
verbenone
FL/FR
caramellic
fenugreek absolute
FL/FR
ethereal
ethyl 4-pentenoate
FL/FR
fatty
(E)-2-
octenal
FL/FR
floral
dihydrorose oxide
FR
dimethyl benzyl carbinyl butyrate
FL/FR
2,4-
dimethyl-3-cyclohexene-1-methanol
FR
geranium oil africa
FL/FR
geranium oil egypt
FL/FR
hexahydrofarnesyl acetone
FL/FR
jasmin pyranol
FR
iso
jasmone
FL/FR
(Z)-
jasmone
FL/FR
neryl formate
FL/FR
2-
pentadecanone
FL/FR
2-
pentyl cyclopentanone
FR
iso
phytol
FL/FR
reseda absolute
FR
rose pyran
FR
fruity
tropical indene
FR
green
iso
butyl benzyl carbinol
FL/FR
iso
butyl heptanoate
FL/FR
iso
butyl methyl ketone
FL/FR
2-sec-
butyl thiazole
FL/FR
heptanal (aldehyde C-7)
FL/FR
1-
heptanol
FL/FR
(Z)-4-
hexen-1-ol
FL/FR
3-
hexenyl 2-methyl butyrate
FL/FR
hexyl hexanoate
FL/FR
english
ivy leaf absolute
FR
seaweed absolute (fucus vesiculosus et serratus)
FL/FR
herbal
6-
acetoxydihydrotheaspirane
FL/FR
alpha-
amyl cinnamyl formate
FL/FR
anethum graveolens herb oil
FL/FR
anthemis nobilis flower oil roman
FL/FR
apium graveolens seed oil india
FL/FR
sweet
basil absolute
FL/FR
3-
butyl phthalide
FL/FR
3-
butylidene phthalide
FL/FR
(+)-alpha-
campholenic aldehyde
FL/FR
celery ketone
FL/FR
celery leaf oil
FL/FR
celery seed oil CO2 extract
FL/FR
celery undecene
FR
dill weed oil cuba
FL/FR
dill weed oil reunion
FL/FR
dimethyl benzyl carbinyl formate
FL/FR
cis-
herbal cyclohexane
FR
herbal dioxane
FR
herbal heptane
FR
hop absolute
FL/FR
hop oil
FL/FR
levisticum officinale herb oil
FL/FR
levisticum officinale root absolute
FL/FR
linalyl formate
FL/FR
linalyl octanoate
FL/FR
marigold oil mexico
FL/FR
melaleuca leucadendron var. cajuputi leaf oil
FL/FR
(E)-6-
methyl-3-hepten-2-one
FL/FR
nonisyl formate
FR
1-
octen-3-yl acetate
FL/FR
origanum oil
FL/FR
origanum oil greece
FL/FR
perillaldehyde
FL/FR
3-
propylidene phthalide
FL/FR
tagete oil CO2 extract
FL/FR
tagete oil south africa
FL/FR
theaspirane
FL/FR
tricyclodecyl acetate
FR
viridiflorol
FL/FR
wormwood oil america
FL/FR
minty
(-)-iso
pulegol
FL/FR
mossy
treemoss absolute
FR
pine
dipentene terpene hydrocarbon byproducts
FR
spicy
iso
butyl angelate
FL/FR
(-)-
cubenol
FL/FR
cuminaldehyde
FL/FR
iso
cyclogeraniol (IFF)
FR
levisticum officinale root oil
FL/FR
tonka
whiskey lactone
FL/FR
woody
amber dodecane
FR
verdoxan
FR
For Flavor
No flavor group found for these
6-
acetoxydihydrotheaspirane
FL/FR
alpha-
amyl cinnamyl formate
FL/FR
iso
butyl heptanoate
FL/FR
3-
butyl phthalide
FL/FR
2-sec-
butyl thiazole
FL/FR
4-
butyl thiazole
FL
dimethyl benzyl carbinyl formate
FL/FR
ethyl 4-pentenoate
FL/FR
fig leaf absolute
FL
(E,E)-2,4-
hexadien-1-ol
FL
melaleuca leucadendron var. cajuputi leaf oil
FL/FR
(E)-6-
methyl-3-hepten-2-one
FL/FR
2-
propyl thiazole
FL
seaweed absolute (fucus vesiculosus et serratus)
FL/FR
verbenone
FL/FR
viridiflorol
FL/FR
alliaceous
alliaceous
cyclopentyl mercaptan
FL
amber
iso
butyl benzyl carbinol
FL/FR
caramellic
fenugreek absolute
FL/FR
celery
3-
butylidene phthalide
FL/FR
cooling
theaspirane
FL/FR
fatty
(E)-2-
octenal
FL/FR
2-
pentadecanone
FL/FR
floral
dimethyl benzyl carbinyl butyrate
FL/FR
geranium oil africa
FL/FR
geranium oil egypt
FL/FR
fruity
hexyl hexanoate
FL/FR
linalyl octanoate
FL/FR
neryl formate
FL/FR
tagete oil CO2 extract
FL/FR
tagete oil south africa
FL/FR
green
angelica root oil
FL/FR
iso
butyl angelate
FL/FR
iso
butyl methyl ketone
FL/FR
(+)-alpha-
campholenic aldehyde
FL/FR
celery ketone
FL/FR
heptanal (aldehyde C-7)
FL/FR
hexahydrofarnesyl acetone
FL/FR
(Z)-4-
hexen-1-ol
FL/FR
3-
hexenyl 2-methyl butyrate
FL/FR
iso
jasmone
FL/FR
1-
octen-3-yl acetate
FL/FR
3-
propylidene phthalide
FL/FR
sorbyl acetate
FL
herbal
anethum graveolens herb oil
FL/FR
anthemis nobilis flower oil roman
FL/FR
apium graveolens seed oil india
FL/FR
sweet
basil absolute
FL/FR
celery leaf oil
FL/FR
celery seed oil CO2 extract
FL/FR
celery seed oleoresin
FL
dill weed oil cuba
FL/FR
dill weed oil reunion
FL/FR
hop absolute
FL/FR
hop oil
FL/FR
linalyl formate
FL/FR
marigold oil mexico
FL/FR
origanum oil
FL/FR
origanum oil greece
FL/FR
curled
parsley seed oleoresin
FL
wormwood oil america
FL/FR
licorice
estragole
FL/FR
minty
(-)-iso
pulegol
FL/FR
oily
iso
phytol
FL/FR
solvent
1-
heptanol
FL/FR
spicy
cinnamyl formate
FL/FR
(-)-
cubenol
FL/FR
cuminaldehyde
FL/FR
levisticum officinale herb oil
FL/FR
levisticum officinale oleoresin
FL
levisticum officinale root absolute
FL/FR
levisticum officinale root oil
FL/FR
perillaldehyde
FL/FR
woody
(Z)-
jasmone
FL/FR
whiskey lactone
FL/FR
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 celery seed
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 dill oil
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 dill root
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 dill root oil
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 dill seed
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 dill shoot
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 fennel seed
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 lovage seed
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 parsley
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 parsley fruit
Search Trop Picture
 parsley fruit oil
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 parsley leaf
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 parsley leaf oil
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 parsley oil
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 parsley rhizome
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 parsley root
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 parsley root oil
Search Trop Picture
 parsley seed
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 parsley seed oil
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 parsley shoot
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 sassafras
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Synonyms:
 allyl dimethoxymethylene dioxybenzene
1-allyl-2,5-dimethoxy-3,4-methylene dioxybenzene
1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene
5-allyl-4,7-dimethoxy-1,3-benzodioxol
 apiol (parsley)
 apioline (parsley)
1,3-benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)-
1,3-benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-
4,7-dimethoxy-5-(2-propenyl)-1,3-benzodioxole
4,7-dimethoxy-5-(prop-2-en-1-yl)-1,3-benzodioxole
4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
4,7-dimethoxy-5-prop-2-enyl-2H-benzo[d]1,3-dioxolene
1,2-methylene dioxy-3,6-dimethoxy-4-allyl benzene
 parsley apiol
 parsley apiole
 parsley camphor
 

Articles:

PubMed:The in vivo antitumor effects on human COLO 205 cancer cells of the 4,7-dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole (apiole) derivative of 5-substituted 4,7-dimethoxy-5-methyl-l,3-benzodioxole (SY-1) isolated from the fruiting body of Antrodia camphorate.
PubMed:Age-dependent changes from allylphenol to prenylated benzoic acid production in Piper gaudichaudianum Kunth.
PubMed:Chemical composition, antimicrobial and antioxidant activities of the essential oil of Psammogeton canescens.
PubMed:[Poisoning by apiole. 3. Toxicological studies: Labat reaction and determination with chromotropic acid].
PubMed:[Poisoning by apiole. II. Histopathological aspects and pathogenetic discussion].
PubMed:[Quantitative determination of apiole].
PubMed:Psychotrophic phenylisopropylamines derived from apiole and dillapiole.
PubMed:Study of the Anti-Proliferative Activity of 5-Substituted 4,7-Dimethoxy-1,3-Benzodioxole Derivatives of SY-1 from Antrodia camphorata on Human COLO 205 Colon Cancer Cells.
PubMed:Medicinal plants from the genus Acalypha (Euphorbiaceae)--a review of their ethnopharmacology and phytochemistry.
PubMed:Endemic Balkan parsnip Pastinaca hirsuta: the chemical profile of essential oils, headspace volatiles and extracts.
PubMed:Critique of medicinal conspicuousness of Parsley(Petroselinum crispum): a culinary herb of Mediterranean region.
PubMed:Chemical composition of the essential oil of Pituranthos scoparius.
PubMed:Chemical and biological evaluation of essential oils from two species of Myrtaceae - Eugenia uniflora L. and Plinia trunciflora (O. Berg) Kausel.
PubMed:Antioxidant capacity and larvicidal and antifungal activities of essential oils and extracts from Piper krukoffii.
PubMed:Acaricidal activities of apiol and its derivatives from Petroselinum sativum seeds against Dermatophagoides pteronyssinus, Dermatophagoides farinae, and Tyrophagus putrescentiae.
PubMed:Chemical composition and antioxidant activities of the essential oil and methanol extracts of Psammogeton canescens.
PubMed:Antimicrobial activities of essential oil and hexane extract of Florence fennel [Foeniculum vulgare var. azoricum (Mill.) Thell.] against foodborne microorganisms.
PubMed:Comparative essential oil composition of flowers, leavesand stems of basil (Ocimum basilicum L.) used as herb.
PubMed:Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components.
PubMed:Essential oil composition of three Peperomia species from the Amazon, Brazil.
PubMed:Chemical composition and antimicrobial activities of the essential oil from the seeds of Enterolobium contortisiliquum (leguminosae).
PubMed:Chemical composition and antimicrobial activity of Momordica charantia seed essential oil.
PubMed:Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris.
PubMed:Inhibition of oxidation of human low-density lipoproteins by phenolic substances in different essential oils varieties.
PubMed:Compartive study of volatile components and fatty acids of plants and in vitro cultures of parsley (Petroselinum crispum (Mill) nym ex hill).
PubMed:Volatile chemical constituents of Piper aduncum L and Piper gibbilimbum C. DC (Piperaceae) from Papua New Guinea.
PubMed:Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus.
PubMed:Plant-derived natural products exhibiting activity against formosan subterranean termites (Coptotermes formosanus).
PubMed:Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol.
PubMed:Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson.
PubMed:Anaerobic utilization of essential oils by denitrifying bacteria.
 
Notes:
crystalline essential oil isolated directly from commercial oil of parsley. Occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill) Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in celery, parsley seeds, and the essential oil of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation.; In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders. It is an irritant and in high doses it is toxic and can cause liver and kidney damage.
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