beta-asarone
cis-2,4,5-trimethoxy-1-propenylbenzene
Identification
| Name | beta-asarone |
| IUPAC | 1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene |
| CAS Number | 5273-86-9 |
| EINECS | 226-096-6 |
| FDA UNII | IGA3MH6IUW |
| Molecular Formula | C12 H16 O3 |
| Molecular Weight | 208.25712000 |
| MDL Number | MFCD00009281 |
| Nikkaji Number | J236.255D |
| Beilstein | 1910605 |
| XlogP3 | 3.00 (est) |
Regulatory
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 |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| IFRA Critical Effect | Carcinogenicity |
| 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 RESTRICTION LIMITS IN THE FINISHED PRODUCT (%) | Category 1: Products applied to the lips |
| Notes | IFRA FLAVOR REQUIREMENTS: |
| Recommendation for beta-asarone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
cis-
asarabacca camphor
(Z)-
asarone
cis-
asarone
cis-iso
asarone
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
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 COâ 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.