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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O
Molecular Weight 256.3826
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BAKUCHIOL

SMILES

CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1

InChI

InChIKey=LFYJSSARVMHQJB-QIXNEVBVSA-N
InChI=1S/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1

HIDE SMILES / InChI

Description

Bakuchiol is a prenylated phenolic monoterpene isolated from Psoralea corylifolia Leguminosae, widely used in Chinese and Indian traditional medicine for the treatment of premature ejaculation, knee pain, alopecia spermatorrhea, enuresis, backache, pollakiuria, vitiligo, callus, and psoriasis. Bakuchiol is shown to have anti-microbial, anti-inflammatory, anti-oxidative, anti-osteoporosis, and anti-depression or anti-stress activities The anti-cancer potential of bakuchiol has been. Bakuchiol inhibits liver cancer cell growth through inducing S phase arrest, caspase 9/3 activation, p53 and Bax up-regulation, as well as Bcl-2 down-regulation. It also inhibits human carboxylesterase 2, which is commonly expressed in tumor tissue and involved in the metabolism of endogenous lipids and drugs.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
77.9 ng/mL
30 mg/kg single, oral
BAKUCHIOL plasma
Rattus norvegicus

AUC

ValueDoseCo-administeredAnalytePopulation
273.6 ng × h/mL
30 mg/kg single, oral
BAKUCHIOL plasma
Rattus norvegicus
4269.2 ng × h/mL
15 mg/kg single, intravenous
BAKUCHIOL plasma
Rattus norvegicus

T1/2

ValueDoseCo-administeredAnalytePopulation
5.9 h
30 mg/kg single, oral
BAKUCHIOL plasma
Rattus norvegicus
7.23 h
15 mg/kg single, intravenous
BAKUCHIOL plasma
Rattus norvegicus

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Rets were treated with bakuchiol at doses of 52.5 and 262.5 mg/kg for 6 weeks.
Route of Administration: Oral
In Vitro Use Guide
The SGC-7901 human gastric cancer cells were seeded on a 96-well plate at 2 × 10^5 cells per well. After 24 h, the cells were treated with bakuchiol at several doses (0, 10, 30, 50, and 100 µM). After incubation times of 12, 24 and 48 h, MTT solution (20 µl) was added. The formazan crystals thus formed were dissolved with DMSO and the absorbance was measured on a microplate reader