alpha-Asarone

Modify Date: 2024-01-02 19:23:56

alpha-Asarone Structure
alpha-Asarone structure
Common Name alpha-Asarone
CAS Number 2883-98-9 Molecular Weight 208.254
Density 1.0±0.1 g/cm3 Boiling Point 296.0±0.0 °C at 760 mmHg
Molecular Formula C12H16O3 Melting Point 57-61 °C(lit.)
MSDS Chinese USA Flash Point 107.7±23.8 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of alpha-Asarone


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]

 Names

Name α-asarone
Synonym More Synonyms

 alpha-Asarone 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
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

 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

 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
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

 Articles28

More 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...

 Synonyms

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
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