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10309-37-2

Basic Information
CAS No.: 10309-37-2
Name: (+)-Bakuchiol
Article Data: 12
Cas Database
Molecular Structure:
Molecular Structure of 10309-37-2 ((+)-Bakuchiol)
Formula: C18H24 O
Molecular Weight: 256.388
Synonyms: Phenol,4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadien-1-yl]-;Bakuchiol(7CI);Phenol, 4-(3-ethenyl-3,7-dimethyl-1,6-octadienyl)-, [S-(E)]-;Phenol,4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadienyl]- (9CI);(S)-(+)-Bakuchiol;(S)-Bakuchiol;Drupanol;UP 256;BAKUCHIOL;Backuchiol;
EINECS: N/A
Density: 0.963g/cm3
Melting Point: N/A
Boiling Point: 391.4°Cat760mmHg
Flash Point: 176.6°C
Solubility: N/A
Appearance: white-off solid or colorless liquid
Hazard Symbols: N/A
Risk Codes: N/A
Safety: Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and fumes.
Transport Information: N/A
PSA: 20.23000
LogP: 5.34410
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  • 4-(3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-PHENOL 10309-37-2

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Uses

 (S)-Bakuchiol is a meroterpen found in the medicinal resinous shrub Psoralea glandulosa. An analogue of Resveratrol (R150000) with antifungal and anti-tumor effects. Studies have shown that Bakuchiol is a potent cytotoxic agent that exhibiting concentration dependent growth inhibition against leukemia cancer cells.

Toxicity Data With Reference

 

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 94mg/kg (94mg/kg)   Mikrobiologicheskii Zhurnal Vol. 42, Pg. 646, 1980.
mouse LD50 intravenous 31mg/kg (31mg/kg)   Mikrobiologicheskii Zhurnal Vol. 42, Pg. 646, 1980.
mouse LD50 oral 2560mg/kg (2560mg/kg)   Mikrobiologicheskii Zhurnal Vol. 42, Pg. 646, 1980.
rat LD subcutaneous > 1gm/kg (1000mg/kg)   Mikrobiologicheskii Zhurnal Vol. 42, Pg. 646, 1980.

Safety Profile

 

Safety Info
HS Code: 2907199090

Specification

Bakuchiol is a meroterpene (a chemical compound having a partial terpenoid structure) in the class terpenophenol. It is found in Psoralea corylifolia and in Otholobium pubescens.
It has been reported to have anticancer activity in pre-clinical models, possibly due to its structural similarity with resveratrol. One study in rats suggested that bakuchiol and ethanol extracts of the Chinese medicinal plant Psoralea corylifolia could protect against bone loss. Bakuchiol isolated from P. corylifolia has shown activity against numerous Gram-positive and Gram-negative oral pathogens. It was able to inhibit the growth of Streptococcus mutans under a range of sucrose concentrations, pH values and in the presence of organic acids in a temperature-dependent manner and also inhibited the growth of cells adhered to a glass surface. Bakuchiol was also found to have retinol functionality.

The (+)-Bakuchiol, with the CAS registry number 10309-37-2,is also known as (S)-(+)-Bakuchiol; (S)-Bakuchiol; Drupanol; UP 256; 4-[(1E,3S)-3-Ethenyl-3,7-dimethyl-1,6-octadien-1-yl]phenol. It belongs to the product categories of Organic matters. This chemical's molecular formula is C18H24O and molecular weight is 256.38. What's more,Its systematic name is 4-(3-Ethenyl-3,7-dimethyl-1,6-octadienyl)phenol.It is usually pale yellow oily liquid,which is the chief component of Psoralea corylifolia Linn.It has antibacterial effects, anti-implantation and estrogen-like effects,and so on.

Physical properties about (+)-Bakuchiol are:
(1)ACD/LogP:  6.546; (2)# of Rule of 5 Violations:  1; (3)ACD/LogD (pH 5.5):  6.55; (4)ACD/LogD (pH 7.4):  6.55; (5)ACD/BCF (pH 5.5):  55562.04; (6)ACD/BCF (pH 7.4):  55452.64; (7)ACD/KOC (pH 5.5):  86674.34; (8)ACD/KOC (pH 7.4):  86503.69; (9)#H bond acceptors:  1; (10)#H bond donors:  1; (11)#Freely Rotating Bonds:  7; (12)Index of Refraction:  1.555; (13)Molar Refractivity:  85.311 cm3; (14)Molar Volume:  265.957 cm3; (15)Surface Tension:  35.8540000915527 dyne/cm; (16)Density:  0.964 g/cm3; (17)Flash Point:  176.59 °C; (18)Enthalpy of Vaporization:  66.602 kJ/mol; (19)Boiling Point:  391.38 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:Oc1ccc(/C=C/[C@@](\C=C)(C)CC\C=C(/C)C)cc1;
(2)Std. InChI: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;
(3)Std. InChIKey:LFYJSSARVMHQJB-QIXNEVBVSA-N.