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(E)-asarone
trans-1,2,4-trimethoxy-5-(1-propenyl)benzene

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Name:1,2,4-trimethoxy-5-[(E)-prop-1-enyl]benzene
CAS Number: 2883-98-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:220-743-6
FDA UNII: DQY9PNE5FK
Nikkaji Web:J70.975A
Beilstein Number:1910605
MDL:MFCD00064457
XlogP3:3.00 (est)
Molecular Weight:208.25712000
Formula:C12 H16 O3
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
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:white to pale yellow crystalline solid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 57.00 to 61.00 °C. @ 760.00 mm Hg
Boiling Point: 296.00 to 297.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.003000 mmHg @ 25.00 °C. (est)
Flash Point: 226.00 °F. TCC ( 107.70 °C. ) (est)
logP (o/w): 3.406 (est)
Soluble in:
 alcohol
 water, 101.8 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
alpha-Asarone 98%
BOC Sciences
For experimental / research use only.
(E)-Asarone >98%
Odor: characteristic
Use: à-Asarone, one of the main psychoactive compounds, with neuroprotective and radioprotective activity in mice, can be used in the synthesis of anti-inflammatory neolignan and in lignan syntheses for antiallergic agents.
ExtraSynthese
For experimental / research use only.
alpha-Asarone (GC) ≥97%
Santa Cruz Biotechnology
For experimental / research use only.
a-Asarone ≥97%
Sigma-Aldrich: Aldrich
For experimental / research use only.
a-Asarone 98%
sds
 
Safety Information:
Preferred SDS: View
 
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-bird - wild LD50 750 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

intraperitoneal-mouse LD50 310 mg/kg
Farmakologiya i Toksikologiya Vol. 48(6), Pg. 17, 1985.

oral-mouse LD50 418 mg/kg
Farmakologiya i Toksikologiya Vol. 48(6), Pg. 17, 1985.

unreported-mouse LD50 176 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 767, 1980.

intravenous-mouse LDLo 66 mg/kg
Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 23, Pg. 52, 1988.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
IFRA Critical Effect:
Carcinogenicity
IFRA fragrance material specification:
 

cis- and trans-Asarone as such should not be used as fragrance ingredients; essential oils containing cis- or trans-asarone (e.g. calamus oils) should not be used at a level such that the total concentration of cis- and trans-asarone exceeds 0.01% in consumer products.

 View the IFRA Standard
View IFRA Standards Library for complete information.
Please review Amendment 49 IFRA documentation for complete information.
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%):
Category 1: Products applied to the lips
See notebox %
Category 2: Products applied to the axillae
See notebox %
Category 3: Products applied to the face/body using fingertips
See notebox %
Category 4: Products related to fine fragrance
See notebox %
 Category 5: Products applied to the face and body using the hands (palms), primarily leave-on
Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on
See notebox %
Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on
See notebox %
Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on
See notebox %
Category 5D: Baby Creams, baby Oils and baby talc
See notebox %
Category 6: Products with oral and lip exposure
See notebox %
 Category 7: Products applied to the hair with some hand contact
Category 7A: Rinse-off products applied to the hair with some hand contact
See notebox %
Category 7B: Leave-on products applied to the hair with some hand contact
See notebox %
Category 8: Products with significant anogenital exposure
See notebox %
Category 9: Products with body and hand exposure, primarily rinse off
See notebox %
 Category 10: Household care products with mostly hand contact
Category 10A: Household care excluding aerosol products (excluding aerosol/spray products)
See notebox %
Category 10B: Household aerosol/spray products
See notebox %
 Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate
Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
See notebox %
Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
See notebox %
Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin
See notebox
 Notes:
IFRA FLAVOR REQUIREMENTS:

Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.

Fragrance ingredient restriction - Note box
On the basis of established maximum concentration levels of this substance in commercially available natural sources (like essential oils, extracts and absolutes), exposure to this substance from the use of these oils and extracts (e.g. Calamus oils) is regarded acceptable as long as the level of cis- and trans-Asarone in the finished consumer product does not exceed 100ppm (0.01 %).
 
Recommendation for (E)-asarone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :636822
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1,2,4-trimethoxy-5-[(E)-prop-1-enyl]benzene
Chemidplus:0002883989
RTECS:DC2975000 for cas# 2883-98-9
 
References:
 1,2,4-trimethoxy-5-[(E)-prop-1-enyl]benzene
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):636822
Pubchem (sid):134982758
Pherobase:View
 
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):C17846
HMDB (The Human Metabolome Database):HMDB31469
FooDB:FDB008006
Export Tariff Code:2909.30.4000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 acorus tatarinowii
Search Trop Picture
 carrot plant
Search Trop Picture
 carrot seed
Search Trop Picture
 cubeb oil @ 1.39%
Data GC Search Trop Picture
 dianthus arenarius
Search Trop Picture
 dianthus monspessulanus
Search Trop Picture
 orthodon dianthera maxim. oil vietnam @ 5.70%
Data GC Search Trop Picture
 
Synonyms:
trans-asarabacca camphor
(E)-isoasarone
alpha-asarone
trans-asarone
trans-isoasarone
trans-asarum camphor
 benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (E)-
 benzene, 1,2,4-trimethoxy-5-[(1E)-1-propen-1-yl]-
 benzene, 1,2,4-trimethoxy-5-[(1E)-1-propenyl]-
 benzene, 1,2,4-trimethoxy-5-propenyl-, (E)-
 etherophenol
trans-1-propenyl-2,4,5-trimethoxybenzene
(E)-1,2,4-trimethoxy-5-(1-propenyl) benzene
(E)-1,2,4-trimethoxy-5-(1-propenyl)benzene
trans-1,2,4-trimethoxy-5-(1-propenyl)benzene
(E)-1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene
1,2,4-trimethoxy-5-[(1E)-1-propen-1-yl]benzene
1,2,4-trimethoxy-5-[(1E)-1-propen-1-yl]benzol
1,2,4-trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene
1,2,4-trimethoxy-5-[(E)-prop-1-enyl]benzene
(E)-1,2,4-trimethoxy-5-prop-1-enylbenzene
(E)-2,4,5-trimethoxypropenyl benzene
trans-2,4,5-trimethoxypropenyl benzene
trans-2,4,5-trimethoxypropenylbenzene
 

Articles:

PubMed:Alpha-Asarone Protects Endothelial Cells from Injury by Angiotensin II.
J-Stage:Cognitive Enhancing Effects of Alpha Asarone in Amnesic Mice by Influencing Cholinergic and Antioxidant Defense Mechanisms
PubMed:Identification of both GABAA receptors and voltage-activated Na(+) channels as molecular targets of anticonvulsant α-asarone.
J-Stage:Anticonvulsant Activity of Acute and Chronic Treatment with a-Asarone from Acorus gramineus in Seizure Models
PubMed:Comparison of the volatile oil composition of three Atalantia species.
J-Stage:Cognitive enhancing effects of alpha asarone in amnesic mice by influencing cholinergic and antioxidant defense mechanisms.
PubMed:Synthesis, antifeedant activity against Coleoptera and 3D QSAR study of alpha-asarone derivatives.
PubMed:α-Asarone Ameliorates Memory Deficit in Lipopolysaccharide-Treated Mice via Suppression of Pro-Inflammatory Cytokines and Microglial Activation.
PubMed:Systemic delivery of alpha-asarone with Kolliphor HS 15 improves its safety and therapeutic effect on asthma.
PubMed:Role of Acorus calamus and alpha-asarone on hippocampal dependent memory in noise stress exposed rats.
PubMed:Simultaneous Determination of Volatile Constituents from Acorus tatarinowii Schott in Rat Plasma by Gas Chromatography-Mass Spectrometry with Selective Ion Monitoring and Application in Pharmacokinetic Study.
PubMed:Reversing P-glycoprotein-mediated multidrug resistance in vitro by α-asarone and β-asarone, bioactive cis-trans isomers from Acorus tatarinowii.
PubMed:An overview on traditional uses and pharmacological profile of Acorus calamus Linn. (Sweet flag) and other Acorus species.
PubMed:Growth-Inhibiting and morphostructural effects of constituents identified in Asarum heterotropoides root on human intestinal bacteria.
PubMed:Chemical compositions, phytotoxicity, and biological activities of Acorus calamus essential oils from Nepal.
PubMed:[Chemical constituents from rhizomes of Acorus tatarinowii].
PubMed:Identification of insecticidal constituents of the essential oil of Acorus calamus rhizomes against Liposcelis bostrychophila Badonnel.
PubMed:Assessment of the genotoxic activity of alpha-asarone and its derivatives in the comet assay.
PubMed:Development of intravenous lipid emulsion of α-asarone with significantly improved safety and enhanced efficacy.
PubMed:Antidepressant-like effects of essential oil and asarone, a major essential oil component from the rhizome of Acorus tatarinowii.
PubMed:Synthesis and antifeedant activity of novel alpha-asarone derivatives against stored-product pests.
PubMed:Development and evaluation of α-asarone transdermal patches based on hot-melt pressure-sensitive adhesives.
PubMed:Metabolism by grasshoppers of volatile chemical constituents from Mangifera indica and Solanum paniculatum leaves.
PubMed:Anticonvulsant activity of acute and chronic treatment with a-asarone from Acorus gramineus in seizure models.
PubMed:Comparative study of the cytotoxicity and genotoxicity of alpha- and Beta-asarone.
PubMed:α-asarone from Acorus gramineus alleviates epilepsy by modulating A-type GABA receptors.
PubMed:Alpha- and beta-asarone in herbal medicinal products. A case study.
PubMed:Cognitive enhancing effects of alpha asarone in amnesic mice by influencing cholinergic and antioxidant defense mechanisms.
PubMed:Separation of cis- and trans-Asarone from Acorus tatarinowii by Preparative Gas Chromatography.
PubMed:Analysis of transformation and excretion of β-asarone in rabbits with GC-MS.
PubMed:Enhanced toxicity of binary mixtures of larvicidal constituents from Asarum heterotropoides root to Culex pipiens pallens (Diptera: Culicidae).
PubMed:[Study on relationship of properties and drug release rate of hot melt pressure sensitive adhesive].
PubMed:Anxiolytic-like effect of α-asarone in mice.
PubMed:Alpha-Asarone incorporated in mixed micelles suitable for intravenous administration: formulation, in-vivo distribution and anaphylaxis study.
PubMed:Chemical composition and biological activity of the volatile extracts of Achillea millefolium.
PubMed:Chemical composition of the essential oil of aerial parts of Haussknechtia elymaitica Boiss. from Iran: a good natural source for trans-asaron.
PubMed:An efficient combination of supercritical fluid extraction and high-speed counter-current chromatography to extract and purify (E)- and (Z)-diastereomers of α-asarone and β-asarone from Acorus tatarinowii Schott.
PubMed:Chemical composition, antinociceptive and anti-inflammatory properties of essential oil from the roots of Illicium lanceolatum.
PubMed:Discovery of gemfibrozil analogues that activate PPARα and enhance the expression of gene CPT1A involved in fatty acids catabolism.
PubMed:Terpenoid composition and antifungal activity of three commercially important essential oils against Aspergillus flavus and Aspergillus niger.
PubMed:Radioprotection by α-asarone: prevention of genotoxicity and hematopoietic injury in mammalian organism.
PubMed:Metabolism mediated interaction of α-asarone and Acorus calamus with CYP3A4 and CYP2D6.
PubMed:Development of drug-in-adhesive transdermal patch for α-asarone and in vivo pharmacokinetics and efficacy evaluation.
PubMed:Neuroprotective effect of honokiol and magnolol, compounds from Magnolia officinalis, on beta-amyloid-induced toxicity in PC12 cells.
PubMed:Activities of α-asarone in various animal seizure models and in biochemical assays might be essentially accounted for by antioxidant properties.
PubMed:Larvicidal activity of Asarum heterotropoides root constituents against insecticide-susceptible and -resistant Culex pipiens pallens and Aedes aegypti and Ochlerotatus togoi.
PubMed:Design, synthesis, and docking of highly hypolipidemic agents: Schizosaccharomyces pombe as a new model for evaluating alpha-asarone-based HMG-CoA reductase inhibitors.
PubMed:Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications.
PubMed:Effects of alpha-asarone on the glutamate transporter EAAC1 in Xenopus oocytes.
PubMed:Neuroprotective effect of alpha-asarone on spatial memory and nitric oxide levels in rats injected with amyloid-beta((25-35)).
PubMed:A high performance liquid chromatography method for simultaneous determination of rosiglitazone and gemfibrozil in human plasma.
PubMed:Chemical composition, oviposition deterrent and larvicidal activities against Aedes aegypti of essential oils from Piper marginatum Jacq. (Piperaceae).
PubMed:2,4,5-trimethoxycinnamic acid: the major metabolite of alpha-asarone, retains most of the pharmacological properties of alpha-asarone.
PubMed:Genotoxicity of alpha-asarone analogues.
PubMed:Preparation and characterization of solid lipid nanoparticles loaded with alpha-Asarone.
PubMed:[Comparison of kinetic behavior in both plasma and tissue after intravenous administration of alpha-asarone in lipid emulsion and aqueous solution in rats and mice].
PubMed:Variability in essential-oil composition of Piper marginatum sensu lato.
PubMed:Rapid determination of volatile constituents in safflower by microwave distillation and simultaneous solid-phase microextraction coupled with gas chromatography-mass spectrometry.
PubMed:[GC-MS analysis of essential oil from nutmeg processed by different traditional methods].
PubMed:[Studies on chemical constituents of green algae Ulva pertusa].
PubMed:[A review of recent ten-year study on alpha-asarone].
PubMed:[Study on alpha-asarone reservoir-type patch].
PubMed:In vitro acetylcholinesterase inhibitory activity of the essential oil from Acorus calamus and its main constituents.
PubMed:Development of self-microemulsifying drug delivery systems for oral bioavailability enhancement of alpha-Asarone in beagle dogs.
PubMed:Effect of alpha-asarone and a derivative on lipids, bile flow and Na+/K+-ATPase in ethinyl estradiol-induced cholestasis in the rat.
PubMed:Hypolipidaemic and antiplatelet activity of phenoxyacetic acid derivatives related to alpha-asarone.
PubMed:Fungicidal property of active component derived from Acorus gramineus rhizome against phytopathogenic fungi.
PubMed:Development of gas chromatography/mass spectrometry following headspace solid-phase microextraction for fast determination of asarones in plasma.
PubMed:Quantitative determination of beta-asarone in calamus by high-performance thin-layer chromatography.
PubMed:3D QSAR study of hypolipidemic asarones by comparative molecular surface analysis.
PubMed:Antioxidant property of alpha-asarone against noise-stress-induced changes in different regions of rat brain.
PubMed:In vitro genotoxic evaluation of three alpha-asarone analogues.
PubMed:Rapid assessment of beta-asarone content of Acorus calamus by micellar electrokinetic capillary chromatography.
PubMed:Molecular docking of the highly hypolipidemic agent alpha-asarone with the catalytic portion of HMG-CoA reductase.
PubMed:Rapid determination of essential oil in Acorus tatarinowii Schott. by pressurized hot water extraction followed by solid-phase microextraction and gas chromatography-mass spectrometry.
PubMed:A new amide from Asarum forbesii Maxim.
PubMed:[Study on GC-MS fingerprint analysis in rhizome of volatile oil of Acorus tatarinowii].
PubMed:Evaluation of analgesic and anti-inflammatory activities of Nectandra megapotamica (Lauraceae) in mice and rats.
PubMed:Inhibition of cyclooxygenase (COX) enzymes by compounds from Daucus carota L. Seeds.
PubMed:Essential oils from two endemic species of Apiaceae from Iran.
PubMed:Alpha-asarone inhibits HMG-CoA reductase, lowers serum LDL-cholesterol levels and reduces biliary CSI in hypercholesterolemic rats.
PubMed:Pest-managing efficacy of trans-asarone isolated from Daucus carota L. seeds.
PubMed:Protection of cultured rat cortical neurons from excitotoxicity by asarone, a major essential oil component in the rhizomes of Acorus gramineus.
PubMed:Synthesis and hypolipidemic activity of modified side chain alpha-asarone homologues.
PubMed:alpha-asarone congeners as hypolipidemic agents. Pseudoreceptor versus minireceptor modeling.
PubMed:Synthesis and hypolipidemic and antiplatelet activities of alpha-asarone isomers in humans (in vitro), mice (in vivo), and rats (in vivo).
PubMed:Dominant lethal study of alpha-asarone in male and female mice after sub-chronic treatment.
PubMed:New studies on trans-anethole oxide and trans-asarone oxide.
PubMed:Synthesis and hypolipidaemic evaluation of a series of alpha-asarone analogues related to clofibrate in mice.
PubMed:Comparison of GC-MS and TLC techniques for asarone isomers determination.
PubMed:Dominant lethal study of alpha-asarone in male mice.
PubMed:Central inhibitory effects of water extract of Acori graminei rhizoma in mice.
PubMed:Hypolipidaemic activity of alpha-asarone in mice.
PubMed:Structure-genotoxicity relationships of allylbenzenes and propenylbenzenes: a quantum chemical study.
PubMed:[Pharmacology and toxicology of Guatteria gaumeri and alpha-asarone].
PubMed:Inhibition of lipid synthesis and secretion in long-term cultures of adult rat hepatocytes by alpha-asarone.
PubMed:alpha-Asarone toxicity in long-term cultures of adult rat hepatocytes.
PubMed:[Teratogenic action of alpha-asarone in the mouse].
PubMed:Sister-chromatid exchange induction produced by in vivo and in vitro exposure to alpha-asarone.
PubMed:Potential allelochemicals fromPistia stratiotes L.
PubMed:Central nervous system studies on an ethanol extract of Acorus calamus rhizomes.
PubMed:[Antianaphylactic components of Asarum forbsii Maxin].
PubMed:[Teratogenic evaluation of alpha-asarone in the rat].
PubMed:Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL/6J x C3H/HeJ F1 mice.
PubMed:[Research on the anticarcinogenic activation of Acorus calcamus. Anticarcinogenic activation of alpha-asarone on human carcinoma cells].
PubMed:[Asarone and its biological properties].
PubMed:Status epilepticus treated by alpha-asarone. Report of 18 cases.
 
Notes:
Constit. of Asarum spp. and carrot seed (Daucus carota) (CCD)
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