.BETA.-ASARONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H16O3
Molecular Weight	208.2536
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(OC)=C(OC)C=C1\C=C/C

InChI

InChIKey=RKFAZBXYICVSKP-WAYWQWQTSA-N

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5-

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28732807
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/29042206 | https://www.ncbi.nlm.nih.gov/pubmed/29032344 | https://www.ncbi.nlm.nih.gov/pubmed/15679319 | https://www.ncbi.nlm.nih.gov/pubmed/25311563 |

α-Asarone is a phytochemical compound with neuroprotective, anti-oxidative, anticonvulsive and cognitive enhancing action, isolated from the Chinese medicinal herb Acorus tatarinowii. Numerous clinical studies in China had indicated the effectiveness of α-asarone against respiratory disorders and epilepsy. Asarone tablets have been clinically used as bronchial asthma and bronchitis prescription drug in China. Unfortunately, toxic and genotoxic studies of a-asarone have indicated that this compound may pose a risk to human health, including embryotoxicity and maternal toxicity in rats, hepatotoxicity in rat-cultivated hepatocytes, and in vivo and in vitro genotoxic damage in mammalian cells.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15679319	Inhibitor 8297		92.3 µM [IC50]
HMG-CoA reductase 47 Target ID: CHEMBL402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25311563	Inhibitor 8297		5.86 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bronchial asthma 50 Sources: http://pubs.rsc.org/-/content/articlelanding/2015/ra/c4ra12049c/unauth#!divAbstract	Primary		Approved 8429	Unknown Approved Use Unknown
Bronchitis 51 Sources: http://pubs.rsc.org/-/content/articlelanding/2015/ra/c4ra12049c/unauth#!divAbstract	Primary		Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Alpha-asarone attenuates depression-like behavior in nicotine-withdrawn mice: Evidence for the modulation of hippocampal pCREB levels during nicotine-withdrawal.	2018 Jan 5	29042206

Patents

Sample Use Guides

In Vivo Use Guide

ICR mice/ Male: 10,15,20, 30, 50 and 100mg/kg i.p. Swiss albino mice/male: 1. 7, 3.5, 7, and 14; p.o.; o.d.× 7 days SD rats/ male: 50, 100 and 200; i.p.; o.d.× 21 days Wistar rats/male: 20 mg/kg, i.v.

Route of Administration: Other

In Vitro Use Guide

BV-2 microglial cells were used for activity evaluation. Cells were cultured in DMEM supplemented with 5% FBS and 50 mkg/mL penicillin-streptomycin in a 37 C humidified incubator supplied with 5% CO2 and 95% O2. The cells were seeded at a density of 5 x 10^4 cells/mL and were pretreated for 1 h with various concentrations of a-asarone (10, 50 and 250 mkM) followed by an incubation with LPS (100 ng/mL) for the indicated times (30 min and 6, 18 and 24 h).

Name

Type

Language

.BETA.-ASARONE

Systematic Name

English

BENZENE, 1,2,4-TRIMETHOXY-5-(1Z)-1-PROPENYL-

Systematic Name

English

CIS-.BETA.-ASARONE

Systematic Name

English

1,2,4-TRIMETHOXY-5-PROPENYLBENZENE, Z-

Systematic Name

English

BETA-ASARONE

Systematic Name

English

CIS-ISOELEMICIN

Systematic Name

English

(Z)-ASARONE

Common Name

English

BENZENE, 1,2,4-TRIMETHOXY-5-PROPENYL-, (Z)-

Common Name

English

BENZENE, 1,2,4-TRIMETHOXY-5-(1-PROPENYL)-, (Z)-

Common Name

English

(Z)-5-PROPENYL-1,2,4-TRIMETHOXYBENZENE

Systematic Name

English

(Z)-1,2,4-TRIMETHOXY-5-(1-PROPENYL)BENZENE

Systematic Name

English

CIS-ISOASARONE

Common Name

English

.BETA.-ASARONE, CIS-

Systematic Name

English

2,4,5-TRIMETHOXYPROPEN-1-YLBENZENE

Systematic Name

English

BENZENE, 1,2,4-TRIMETHOXY-5-(1Z)-1-PROPEN-1-YL-

Systematic Name

English

Classification Tree Code System Code

JECFA EVALUATION

BETA-ASARONE