alpha-Asarone

Names

[ Name ]:
alpha-Asarone

[Synonym ]:
Benzene, 1,2,4-trimethoxy-5-[(1E)-1-propen-1-yl]-
trans-1,2,4-Trimethoxy-5-(1-propenyl)benzene
Asarin
1,2,4-trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene
EINECS 220-743-6
A-Asarion
trans-1,2,4-Trimethoxy-5-(1-propenyl)benzene,trans-1-Propenyl-2,4,5-trimethoxybenzene
Asaron
alpha-asarone
(E)-Asarone
benzene, 1,2,4-trimethoxy-5-[(1E)-1-propenyl]-
a-Asarone
α-Asarone
1,2,4-Trimethoxy-5-[(1E)-1-propen-1-yl]benzene
ASARONE,A
MFCD00064457
1,2,4-Triméthoxy-5-[(1E)-1-propèn-1-yl]benzène
trans-Asarone
trans-2,4,5-trimethoxyphenylpropene
Asarone
trans-asaron
Etherophenol

Biological Activity

[Description]:

Alpha-Asarone is one of the main psychoactive compounds, and possesses an antidepressant-like activity in mice.IC50 value:Target:In vitro: The results indicated that α-asarone significantly attenuated the LPS-stimulated increase in neuroinflammatory responses and suppressed pro-inflammatory cytokine production in BV-2 cells. Mechanistic study revealed that α-asarone?inhibited the LPS-stimulated activation via regulation of nuclear factor kappa-B by blocking degradation of inhibitor kappa B-alpha signaling in BV-2 microglial cells. [2]In vivo: The present results reveal that the acute treatment of α-asarone elicited biphasic responses on immobility such that the duration of the immobility time is significantly reduced at lower doses (15 and 20 mg/kg, i.p.) but increased at higher doses (50 and 100 mg/kg, i.p.) in the TST. Besides, α-asarone at higher doses (50 and 100 mg/kg, i.p.) significantly decreased the spontaneous locomotor activity.[1]

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Research Areas >> Neurological Disease

Natural Products >> Phenylpropanoids

[References]

[1]. Ranjithkumar Chellian, et al. Biphasic Effects of α-Asarone on Immobility in the Tail Suspension Test: Evidence for the Involvement of the Noradrenergic and Serotonergic Systems in Its Antidepressant-Like Activity. Front Pharmacol. 2016; 7: 72.

[2]. Byung-Wook Kim, et al. α-Asarone attenuates microglia-mediated neuroinflammation by inhibiting NF kappa B activation and mitigates MPTP-induced behavioral deficits in a mouse model of Parkinson's disease. Neuropharmacology, Volume 97, October 2015, Pages

[3]. Hye-Jung Park, et al. Effect of α-asarone on angiogenesis and matrix metalloproteinase. Environmental Toxicology and Pharmacology, Volume 39, Issue 3, May 2015, Pages 1107–1114

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
296.0±0.0 °C at 760 mmHg

[ Melting Point ]:
57-61 °C(lit.)

[ Molecular Formula ]:
C₁₂H₁₆O₃

[ Molecular Weight ]:
208.254

[ Flash Point ]:
107.7±23.8 °C

[ Exact Mass ]:
208.109940

[ PSA ]:
27.69000

[ LogP ]:
2.98

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.526

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DC2975000

CHEMICAL NAME :: Benzene, 1,2,4-trimethoxy-5-propenyl-, (E)-

CAS REGISTRY NUMBER :: 2883-98-9

BEILSTEIN REFERENCE NO. :: 1910606

LAST UPDATED :: 199612

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C12-H16-O3

MOLECULAR WEIGHT :: 208.28

WISWESSER LINE NOTATION :: 2U1R BO1 DO1 EO1 -T

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 418 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 310 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 66 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 176 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - wild bird species

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 156 mg/kg

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 600 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: Mutation test systems - not otherwise specified

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 279,269,1992 *** REVIEWS *** TOXICOLOGY REVIEW RICLAG Revista de Investigacion Clinica. (Instituto Nacional de la Nutricion Salvador Zubiran, Vasco de Quiroga No. 15, Deleq. Tlalpan, 14000 Mexico City, Mexico) V.1- 1948- Volume(issue)/page/year: 45,597,1993

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DC2975000

[ Packaging Group ]:
II; III

[ Hazard Class ]:
4.1

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

β-Asarone, an active principle of Acorus calamus rhizome, inhibits morphogenesis, biofilm formation and ergosterol biosynthesis in Candida albicans.

Phytomedicine 20(2) , 139-42, (2013)

Anti-Candida potential of Acorus calamus rhizome and its active principle, β-asarone, was evaluated against the human fungal pathogen, Candida albicans. β-Asarone exhibited promising growth inhibitory...

Cerebrovascular protection of β-asarone in Alzheimer's disease rats: a behavioral, cerebral blood flow, biochemical and genic study.

J. Ethnopharmacol. 144(2) , 305-12, (2012)

Recent studies have suggested that β-asarone have neuroprotective and cardiovascular protective effects in animal model. However, the influence of β-asarone on cerebrovascular system has not been expl...

Simultaneous determination ofα-,β- andγ-asarone inAcorus tatarinowiiby microemulsion electrokinetic chromatography with [BMIM]PF6as oil phase

Talanta 101 , 510-5, (2012)

In the present study, a rapid and repeatable microemulsion electrokinetic chromatography (MEEKC) method was developed for the simultaneous determination of three isomers (α-, β- and γ-asarone) in Acor...