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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 of .BETA.-ASARONE

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-

HIDE SMILES / InChI

Molecular Formula C12H16O3
Molecular Weight 208.2536
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
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

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available

Originator

Sources: Berichte der Deutschen Chemischen Gesellschaft 22, 3172-6

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
92.3 µM [IC50]
5.86 µM [IC50]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:16:57 GMT 2023
Edited
by admin
on Fri Dec 15 20:16:57 GMT 2023
Record UNII
IGA3MH6IUW
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 20:16:57 GMT 2023 , Edited by admin on Fri Dec 15 20:16:57 GMT 2023
Code System Code Type Description
PUBCHEM
5281758
Created by admin on Fri Dec 15 20:16:57 GMT 2023 , Edited by admin on Fri Dec 15 20:16:57 GMT 2023
PRIMARY
CAS
5273-86-9
Created by admin on Fri Dec 15 20:16:57 GMT 2023 , Edited by admin on Fri Dec 15 20:16:57 GMT 2023
PRIMARY
EPA CompTox
DTXSID601020057
Created by admin on Fri Dec 15 20:16:57 GMT 2023 , Edited by admin on Fri Dec 15 20:16:57 GMT 2023
PRIMARY
ECHA (EC/EINECS)
226-096-6
Created by admin on Fri Dec 15 20:16:57 GMT 2023 , Edited by admin on Fri Dec 15 20:16:57 GMT 2023
PRIMARY
CHEBI
10353
Created by admin on Fri Dec 15 20:16:57 GMT 2023 , Edited by admin on Fri Dec 15 20:16:57 GMT 2023
PRIMARY
WIKIPEDIA
ASARONE
Created by admin on Fri Dec 15 20:16:57 GMT 2023 , Edited by admin on Fri Dec 15 20:16:57 GMT 2023
PRIMARY
FDA UNII
IGA3MH6IUW
Created by admin on Fri Dec 15 20:16:57 GMT 2023 , Edited by admin on Fri Dec 15 20:16:57 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
In view of the toxic properties documented for the oil and associated with beta-asarone, it has been recommended that only beta-asarone-free calamus root should be used in phytotherapy.