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Related CAS#:
17015-60-0 10309-37-2
1020108-62-6 10309-44-1
17015-63-3

10309-37-2

10309-37-2 structure
10309-37-2 structure
  • Name: Bakuchiol
  • Chemical Name: 4-(3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl)phenol
  • CAS Number: 10309-37-2
  • Molecular Formula: C18H24O
  • Molecular Weight: 256.383
  • Catalog: Natural product Phenols
  • Create Date: 2018-07-29 12:32:14
  • Modify Date: 2024-01-02 11:45:45
  • Bakuchiol is a phytoestrogen isolated from the seeds of Psoralea corylifolia L; has anti-tumor effects.IC50 value:Target:in vitro: Bakuchiol reduced mitochondrial membrane potential (Psim) of cells in a concentration- and time-dependent manner, showing a more potent effect than that of resveratrol. S phase arrest, caspase 9/3 activaton, p53 and Bax up-regulation, as well as Bcl-2 down-regulation were observed in bakuchiol-treated A549 cells [1]. UGT2B7 was inhibited by the strongest intensity. The noncompetitive inhibition was demonstrated by the results obtained from Dixon plot and Lineweaver-Burk plot. The Ki value was calculated to be 10.7 μM [2]. Bakuchiol was found to be naturally occurring potent inhibitors of hCE2, with low Ki values ranging from 0.62μM to 3.89μM [3]. After exposure to bakuchiol at 0.25-fold, 0.5-fold and 1-fold of minimum inhibitory concentration (MIC) (3.91 μg/ml) for 24h, the fungal conidia of T. mentagrophytes demonstrated a significant dose-dependent increase in membrane permeability. Moreover, bakuchiol at 1-fold MIC elicited a 187% elevation in reactive oxygen species (ROS) level in fungal cells after a 3-h incubation [4].in vivo: In combination with the reported concentration after an intravenous administration of bakuchiol (15 mg/kg) in rats, the high risk of in vivo inhibition of bakuchiol towards UGT2B7-catalyzed metabolism of drugs was indicated [2]. In a guinea pig model of tinea pedis, bakuchiol at 1%, 5% or 10% (w/w) concentration in aqueous cream could significantly reduce the fungal burden of infected feet (p<0.01-0.05) [4].
Name 4-(3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl)phenol
Synonyms P-(3,7-dimethyl-3-vinylocta-trans-1,6-dimethyl) phenol
Phenol, 4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadien-1-yl]-
BACTRIS GASIPAES FRUIT JUICE
4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol
Backuchiol
Bakuchiol
4-[(1E,3S)-3,7-Dimethyl-3-vinyl-1,6-octadien-1-yl]phenol
Drupanol
4-[(1E,3S)-3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl]phenol
(S)-bakuchiol
UP 256
Phenol, 4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadienyl]-
Description Bakuchiol is a phytoestrogen isolated from the seeds of Psoralea corylifolia L; has anti-tumor effects.IC50 value:Target:in vitro: Bakuchiol reduced mitochondrial membrane potential (Psim) of cells in a concentration- and time-dependent manner, showing a more potent effect than that of resveratrol. S phase arrest, caspase 9/3 activaton, p53 and Bax up-regulation, as well as Bcl-2 down-regulation were observed in bakuchiol-treated A549 cells [1]. UGT2B7 was inhibited by the strongest intensity. The noncompetitive inhibition was demonstrated by the results obtained from Dixon plot and Lineweaver-Burk plot. The Ki value was calculated to be 10.7 μM [2]. Bakuchiol was found to be naturally occurring potent inhibitors of hCE2, with low Ki values ranging from 0.62μM to 3.89μM [3]. After exposure to bakuchiol at 0.25-fold, 0.5-fold and 1-fold of minimum inhibitory concentration (MIC) (3.91 μg/ml) for 24h, the fungal conidia of T. mentagrophytes demonstrated a significant dose-dependent increase in membrane permeability. Moreover, bakuchiol at 1-fold MIC elicited a 187% elevation in reactive oxygen species (ROS) level in fungal cells after a 3-h incubation [4].in vivo: In combination with the reported concentration after an intravenous administration of bakuchiol (15 mg/kg) in rats, the high risk of in vivo inhibition of bakuchiol towards UGT2B7-catalyzed metabolism of drugs was indicated [2]. In a guinea pig model of tinea pedis, bakuchiol at 1%, 5% or 10% (w/w) concentration in aqueous cream could significantly reduce the fungal burden of infected feet (p<0.01-0.05) [4].
Related Catalog
References

[1]. Chen Z, et al. Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line. Eur J Pharmacol. 2010 Sep 25;643(2-3):170-9.

[2]. Xu Y, et al. In vitro evidence for bakuchiol's influence towards drug metabolism through inhibition of UDP-glucuronosyltransferase (UGT) 2B7. Afr Health Sci. 2014 Sep;14(3):564-9.

[3]. Li YG, et al. Fructus Psoraleae contains natural compounds with potent inhibitory effects towards human carboxylesterase 2. Fitoterapia. 2015 Jan 13;101C:99-106.

[4]. Lau KM, et al. Anti-dermatophytic activity of bakuchiol: in vitro mechanistic studies and in vivo tinea pedis-inhibiting activity in a guinea pig model. Phytomedicine. 2014 Jun 15;21(7):942-5.
Density 1.0±0.1 g/cm3
Boiling Point 391.4±21.0 °C at 760 mmHg
Molecular Formula C18H24O
Molecular Weight 256.383
Flash Point 176.6±11.7 °C
Exact Mass 256.182709
PSA 20.23000
LogP 6.40
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.555

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SL3785000
CHEMICAL NAME :
Phenol, 4-(3-ethenyl-3,7-dimethyl-1,6-octadienyl)-, (S-(E))-
CAS REGISTRY NUMBER :
10309-37-2
LAST UPDATED :
199801
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C18-H24-O
MOLECULAR WEIGHT :
256.42
WISWESSER LINE NOTATION :
QR D1U1X1&1U1&3UY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2560 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
94 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
31 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2500 mg/kg/10D-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
REFERENCE :
MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980
Hazard Codes F+
RIDADR NONH for all modes of transport
RTECS SL3785000
HS Code 2907199090
HS Code 2907199090
Summary 2907199090 other monophenols VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

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