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beta-asarone
cis-2,4,5-trimethoxy-1-propenylbenzene

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Name:1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene
CAS Number: 5273-86-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:226-096-6
FDA UNII:IGA3MH6IUW
Nikkaji Web:J236.255D
Beilstein Number:1910605
MDL:MFCD00009281
XlogP3:3.00 (est)
Molecular Weight:208.25712000
Formula:C12 H16 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome 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
 
Physical Properties:
Appearance:colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:1.07300 @ 25.00 °C.
Refractive Index:1.56100 @ 20.00 °C.
Melting Point: 62.00 to 63.00 °C. @ 760.00 mm Hg
Boiling Point: 264.00 to 267.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.003000 mmHg @ 25.00 °C. (est)
Flash Point:> 230.00 °F. TCC ( > 110.00 °C. )
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:
BOC Sciences
For experimental / research use only.
beta-Asarone 98%
Odor: characteristic
Use: b-Asarone isolated from the herbs of Asarum sieboldii Miq. It might be developed as a promising candidate to treat various neuroinflammatory diseases. anti-inflammatory effects
Coompo
For experimental / research use only.
beta-Asarone from Plants ≥96%
Odor: characteristic
Use: β-Asarone can affect the central nervous system. β-Asarone could attenuate neuronal apoptosis in rat hippocampus and might be a potential candidate for development as a therapeutic agent to manage cognitive impairment associated with conditions such as Alzheimer’s disease. Other authors found β-Asarone could reduce the toxicity of excitatory amino acids and increase the expression of c-fos in the epileptic rat brain. In addition, β-Asarone could reduce the injuries of blood vessel endothelium and nerve cells of the cortex and improve the cognitive function of the beta-amyloid hippocampus injection rats. Complement β-Asarone is protective against cerebral ischemia in specific way. The administration of β-Asarone could reduce focal cerebral ischemic/reperfusion injury. The Mechanism of β-Asarone in protection of cerebral ischemia was via increasing antioxidants activity related to lesion pathogenesis.
ExtraSynthese
For experimental / research use only.
beta-Asarone (GC) ≥95%
Sigma-Aldrich: Aldrich
For experimental / research use only.
cis-2,4,5-Trimethoxy-1-propenylbenzene 70%
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
S 02 - Keep out of the reach of children.
S 23 - Do not breath vapour.
S 24/25 - Avoid contact with skin and eyes.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
 
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:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: natural substances and extractives
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.

IFRA: View Standard
limits in the finished product for - "leave on the skin contact":
  0.0100 % Restriction.
limits in the finished product for - "wash off the skin contact":
  0.0100 % Restriction.
limits in the finished product for - "no skin contact":
  0.0100 % Restriction.
Recommendation for beta-asarone usage levels up to:
 PROHIBITED: Should not be used as a fragrance ingredient.
 
Recommendation for beta-asarone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
Env. Mutagen Info. Center:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281758
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene
Chemidplus:0005273869
RTECS:DC3000000 for cas# 5273-86-9
 
References:
 1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281758
Pubchem (sid):134984836
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (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):C10430
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2909.30.4000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 calamus rhizome oil @ 2.85%
Data GC Search Trop Picture
 calamus root oil @ 1.68%
Data GC Search Trop Picture
 carrot seed oil @ 17.65%
Data GC Search Trop Picture
 helichrysum arenarium (l.) moench oil hungary @ 1.50%
Data GC Search Trop Picture
 mangrove bark red oil cuba @ trace%
Data GC Search Trop Picture
 orthodon dianthera maxim. oil vietnam @ 5.50%
Data GC Search Trop Picture
 ylang ylang oil CO2 extract @ 0.02%
Data GC Search Trop Picture
 
Synonyms:
cis-asarabacca camphor
(Z)-asarone
cis-asarone
cis-isoasarone
cis-asarum camphor
 benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (Z)-
 benzene, 1,2,4-trimethoxy-5-[(1Z)-1-propen-1-yl]-
 benzene, 1,2,4-trimethoxy-5-propenyl-, (Z)-
(Z)-5-propenyl-1,2,4-trimethoxybenzene
cis-1-propenyl-2,4,5-trimethoxybenzene
cis-2,4,5-trimethoxy-1-propenylbenzene
(Z)-1,2,4-trimethoxy-5-(1-propenyl) benzene
(Z)-1,2,4-trimethoxy-5-(1-propenyl)benzene
1,2,4-trimethoxy-5-[(1Z)-1-propen-1-yl]benzene
1,2,4-trimethoxy-5-[(1Z)-1-propen-1-yl]benzol
1,2,4-trimethoxy-5-[(1Z)-prop-1-en-1-yl]benzene
1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene
(Z)-2,4,5-trimethoxypropen-1-yl benzene
cis-2,4,5-trimethoxypropenyl benzene
cis-2,4,5-trimethoxypropenylbenzene
 

Articles:

PubMed:The Efficacy of Essential Oils as Natural Preservatives in Vegetable Oil.
J-Stage:Beta-Asarone Attenuates Neuronal Apoptosis Induced by Beta Amyloid in Rat Hippocampus
PubMed:Role of Acorus calamus and alpha-asarone on hippocampal dependent memory in noise stress exposed rats.
J-Stage:Beta-Asarone Improves Cognitive Function by Suppressing Neuronal Apoptosis in the Beta-Amyloid Hippocampus Injection Rats
PubMed:β-Asarone prevents autophagy and synaptic loss by reducing ROCK expression in asenescence-accelerated prone 8 mice.
PubMed:Molecular and chemical profiling of 'sweet flag' (Acorus calamus L.) germplasm from India.
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:Beta-asarone, a major component of Acorus tatarinowii Schott, attenuates focal cerebral ischemia induced by middle cerebral artery occlusion in rats.
PubMed:The Rhizomes of Acorus gramineus and the Constituents Inhibit Allergic Response In vitro and In vivo.
PubMed:Fate of β-asarone in Ayurvedic Sodhana process of Vacha.
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:Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: structure-activity relationship.
PubMed:Consumer and farmer safety evaluation of application of botanical pesticides in black pepper crop protection.
PubMed:Antidepressant-like effects of essential oil and asarone, a major essential oil component from the rhizome of Acorus tatarinowii.
PubMed:β-Asarone induces senescence in colorectal cancer cells by inducing lamin B1 expression.
PubMed:Gas chromatography-mass spectrometry analysis on compounds in volatile oils extracted from yuan zhi (radix polygalae) and shi chang pu (acorus tatarinowii) by supercritical CO2.
PubMed:Beta-asarone induces LoVo colon cancer cell apoptosis by up-regulation of caspases through a mitochondrial pathway in vitro and in vivo.
PubMed:β-Asarone, an active principle of Acorus calamus rhizome, inhibits morphogenesis, biofilm formation and ergosterol biosynthesis in Candida albicans.
PubMed:Metabolism by grasshoppers of volatile chemical constituents from Mangifera indica and Solanum paniculatum leaves.
PubMed:β-Asarone inhibits neuronal apoptosis via the CaMKII/CREB/Bcl-2 signaling pathway in an in vitro model and AβPP/PS1 mice.
PubMed:Comparative study of the cytotoxicity and genotoxicity of alpha- and Beta-asarone.
PubMed:Cerebrovascular protection of β-asarone in Alzheimer's disease rats: a behavioral, cerebral blood flow, biochemical and genic study.
PubMed:Alpha- and beta-asarone in herbal medicinal products. A case study.
PubMed:A rapid HPLC-ESI-MS/MS method for determination of β-asarone, a potential anti-epileptic agent, in plasma after oral administration of Acorus calamus extract to rats.
PubMed:β-Asarone protects PC12 cells against OGD/R-induced injury via attenuating Beclin-1-dependent autophagy.
PubMed:Pharmacokinetics of beta-asarone in rabbit blood, hippocampus, cortex, brain stem, thalamus and cerebellum.
PubMed:Analysis of transformation and excretion of β-asarone in rabbits with GC-MS.
PubMed:Beta-asarone attenuates ischemia-reperfusion-induced autophagy in rat brains via modulating JNK, p-JNK, Bcl-2 and Beclin 1.
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:Supercritical fluid CO₂ extraction of Acorus calamus L. (Arales: Araceae) and its contact toxicity to Sitophilus zeamais Motschusky (Coleoptera: Curculionidae).
PubMed:A solid-phase microextraction GC/MS/MS method for rapid quantitative analysis of food and beverages for the presence of legally restricted biologically active flavorings.
PubMed:Phenolic constituents of Acorus gramineus.
PubMed:Terpenoid composition and antifungal activity of three commercially important essential oils against Aspergillus flavus and Aspergillus niger.
PubMed:Insecticidal effect and chemical composition of the volatile oil from Bergenia ligulata.
PubMed:Beta-asarone inhibits synaptic inputs to airway preganglionic parasympathetic motoneurons.
PubMed:Brazilian red propolis: unreported substances, antioxidant and antimicrobial activities.
PubMed:Positive GABA(A) receptor modulators from Acorus calamus and structural analysis of (+)-dioxosarcoguaiacol by 1D and 2D NMR and molecular modeling.
PubMed:Beta-asarone attenuates beta-amyloid-induced apoptosis through the inhibition of the activation of apoptosis signal-regulating kinase 1 in SH-SY5Y cells.
PubMed:Quality assessment of a formulated Chinese herbal decoction, Kaixinsan, by using rapid resolution liquid chromatography coupled with mass spectrometry: A chemical evaluation of different historical formulae.
PubMed:Neuroprotective effect of honokiol and magnolol, compounds from Magnolia officinalis, on beta-amyloid-induced toxicity in PC12 cells.
PubMed:Reinvestigation of structure-activity relationship of methoxylated chalcones as antimalarials: synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone.
PubMed:[Study on the chemical constituents of Humulus scandens].
PubMed:Beta-asarone attenuates neuronal apoptosis induced by Beta amyloid in rat hippocampus.
PubMed:Beta-asarone improves cognitive function by suppressing neuronal apoptosis in the beta-amyloid hippocampus injection rats.
PubMed:[Chemical constituents from petroleum ether fraction of ethanol extract of Acorus tatarinowii].
PubMed:[Research on liposoluble ingredients of Quchiling].
PubMed:Beta-asarone protection against beta-amyloid-induced neurotoxicity in PC12 cells via JNK signaling and modulation of Bcl-2 family proteins.
PubMed:Larvicidal and structure-activity studies of natural phenylpropanoids and their semisynthetic derivatives against the tobacco armyworm Spodoptera litura (Fab.) (Lepidoptera: Noctuidae).
PubMed:Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications.
PubMed:Reduction of beta-asarone in acori rhizoma by decoction.
PubMed:Compositional variations and anthelmentic activity of essential oils from rhizomes of different wild populations of Acorus calamus L. and its major component, beta-Asarone.
PubMed:Supplemental ultraviolet-B induced changes in essential oil composition and total phenolics of Acorus calamus L. (sweet flag).
PubMed:A high performance liquid chromatography method for simultaneous determination of rosiglitazone and gemfibrozil in human plasma.
PubMed:Fumigant antifungal activity of essential oil components from Acorus gramineus against three phytopathogenic fungi.
PubMed:Volatiles from leaves and rhizomes of Fragrant Acorus spp. (Acoraceae).
PubMed:Nematicidal activity of plant essential oils and components from coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii) essential oils against pine wood nematode (Bursaphelenchus xylophilus).
PubMed:[Effects of beta-asarone on expression of FOS and GAD65 in cortex of epileptic rat induced by penicillin].
PubMed:[Effects of beta-asarone on expression of c-fos in kindling epilepsy rat brain].
PubMed:Systematic study of beta-asarone-rich volatile oil from Acori graminei rhizoma by off-line supercritical CO2 extraction-gas chromatography-mass spectrometry.
PubMed:Rapid determination of volatile constituents in safflower by microwave distillation and simultaneous solid-phase microextraction coupled with gas chromatography-mass spectrometry.
PubMed:[Studies on chemical constituents of green algae Ulva pertusa].
PubMed:[Protective effects of beta-asarone on cultured rat cortical neurons damage induced by glutamate].
PubMed:[Effects of beta-asarone on morphology and cell viability in PC12 cells and cultured rat cortical neurons].
PubMed:A fraction of Acorus calamus L. extract devoid of beta-asarone enhances adipocyte differentiation in 3T3-L1 cells.
PubMed:In vitro acetylcholinesterase inhibitory activity of the essential oil from Acorus calamus and its main constituents.
PubMed:[Effects of annao tablet on S100B and NPY of cortex in chronic epilepsy rats].
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:Chemical composition of the essential oil and supercritical CO2 extract of Commiphora myrrha (Nees) Engl. and of Acorus calamus L.
PubMed:Antioxidative activity of volatile extracts isolated from Angelica tenuissimae roots, peppermint leaves, pine needles, and sweet flag leaves.
PubMed:Identification of an EcoRI restriction site for a rapid and precise determination of beta-asarone-free Acorus calamus cytotypes.
PubMed:Rapid assessment of beta-asarone content of Acorus calamus by micellar electrokinetic capillary chromatography.
PubMed:[Pharmacokinetics of beta-asarone in rats].
PubMed:[Study on GC-MS fingerprint analysis in rhizome of volatile oil of Acorus tatarinowii].
PubMed:Ultrasound-assisted conversion of toxic beta-asarone into nontoxic bioactive phenylpropanoid: isoacoramone, a metabolite of Piper marginatum and Acorus tararinowii.
PubMed:Antifungal activity of beta-asarone from rhizomes of Acorus gramineus.
PubMed:[Effects of beta-asaron on gene expression in mouse brain].
PubMed:Rhizoma acori graminei and its active principles protect PC-12 cells from the toxic effect of amyloid-beta peptide.
PubMed:Protection of cultured rat cortical neurons from excitotoxicity by asarone, a major essential oil component in the rhizomes of Acorus gramineus.
PubMed:A mild and convenient procedure for the conversion of toxic beta-asarone into rare phenylpropanoids: 2,4,5-trimethoxycinnamaldehyde and gamma-asarone.
PubMed:[New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)].
PubMed:One step conversion of toxic beta-asarone from Acorus calamus into 1-(2,4,5-trimethoxyphenyl)-1,2-dihydroxypropane and asaronaldehyde occurring in Piper clusii.
PubMed:Micronucleus formation in human lymphocytes and in the metabolically competent human hepatoma cell line Hep-G2: results with 15 naturally occurring substances.
PubMed:Insecticidal activity against Aedes aegypti larvae of some medicinal South American plants.
PubMed:Antifungal and larvicidal compounds from the root bark of Cordia alliodora.
PubMed:SOS induction of selected naturally occurring substances in Escherichia coli (SOS chromotest).
PubMed:DNA profiling of Acorus calamus chemotypes differing in essential oil composition.
PubMed:Comparison of GC-MS and TLC techniques for asarone isomers determination.
PubMed:Mobility inhibition and nematocidal activity of asarone and related phenylpropanoids on second-stage larvae of Toxocara canis.
PubMed:Genotoxicity of the alkenylbenzenes alpha- and beta-asarone, myristicin and elimicin as determined by the UDS assay in cultured rat hepatocytes.
PubMed:Structure-genotoxicity relationships of allylbenzenes and propenylbenzenes: a quantum chemical study.
PubMed:The anticoagulant effect of beta-asarone in the mouse and the rat.
PubMed:Asarones fromAcorus calamus L. Oil : Their effect on feeding behavior and dietary utilization inPeridroma saucia.
PubMed:[Antianaphylactic components of Asarum forbsii Maxin].
PubMed:Determination of beta-asarone, safrole, isosafrole and anethole in alcoholic drinks by high-performance liquid chromatography.
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:Spasmolytische wirkung des isoasaronfreien kalmus1.
PubMed:Quantitative analysis of alpha, beta-thujone, pulegone, safrole, coumarin and beta-asarone in alcoholic beverages by selected-ion monitoring.
PubMed:Mutagenicity testing of beta-asarone and commercial calamus drugs with Salmonella typhimurium.
PubMed:[Extraction of thermolabile compounds with supercritical gases.].
PubMed:[Composition of the essential oil from beta-Asarone free calamus.].
PubMed:[To the classification of commercial Calamus drugs].
PubMed:[Use of the mass spectrometer as a specific detector in the analysis of alcoholic beverages by gas-liquid chromatography].
PubMed:Gas-liquid chromatographic determination of beta-asarone in wine: collaborative study.
PubMed:Spectrofluorometric determination of beta-asarone in sweet and dry vermouths.
PubMed:Gas-liquid chromatographic determination of beta-asarone in wines and flavors.
PubMed:[Thin-layer cromatographic and densitometric evaluation of beta-asarone in alcoholic flavored beverages (author's transl)].
PubMed:Effects of asarone and beta-asarone on conditioned responses, fighting behaviour and convulsions.
PubMed:Studies on Acorus calamus. VI. Pharmacological actions of asarone and beta-asarone on cardiovascular system and smooth muscles.
PubMed:Studies on Acorus calamus. V. Pharmacological actions of asarone and beta-asarone on central nervous system.
PubMed:Pharmacodynamical effects of asarone and beta-asarone.
 
Notes:
None found
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