CAS Number10309-37-2
SynonymsP-(3,7-dimethyl-3-vinylocta-trans-1,6-dimethyl) phenol; 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
Molecular FormulaC18H24O
Molecular Weight256.38
Purity≥95%
Density1.0±0.1 g/cm3
Boiling Point391.4±21.0 °C at 760 mmHg
Appearanceliquid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 10309-37-2 |
| Catalog No. | 2A-9065764 |
| Chinese Name | 补骨脂酚 |
| Synonyms | P-(3,7-dimethyl-3-vinylocta-trans-1,6-dimethyl) phenol; 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 |
| Molecular Formula | C18H24O |
| Molecular Weight | 256.38 |
| Purity | ≥95 |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 391.4±21.0 °C at 760 mmHg |
| Appearance | liquid |
| Storage Condition | Ventilated and low temperature drying |
| Application | Bakuchiol is a phytoestrogen derived from psoralen seeds and has anti-tumor and other effects. |
| HTC | 2907199090 |
| PubChem ID | 329825075 |
| MDL Number | MFCD01707441 |
| SMILES | C\C(C)=C/CC[C@@](C)(C=C)\C=C\c1ccc(O)cc1 |
| 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 |
| InChI Key | LFYJSSARVMHQJB-QIXNEVBVSA-N |
| Beilstein/REAXYS | 3611720 |
| NACRES Code | NA.25 |
| UNSPSC | 12352205 |
| Hazard Symbols | transportation |
| MSDS | msds/65764_1_10309_37_2.pdf |
| Bioactivity | 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 Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK Research Areas >> Cancer Natural Products >> Terpenoids and Glycosides 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. Chemical & Physical Properties 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 InChIKey LFYJSSARVMHQJB-QIXNEVBVSA-N SMILES C=CC(C)(C=Cc1ccc(O)cc1)CCC=C(C)C |
| Use of | Properties Articles25 Name 4-(3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl)phenol Synonym More Synonyms Bakuchiol Biological Activity Related Catalog Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK Research Areas >> Cancer Natural Products >> Terpenoids and Glycosides References [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. [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. Chemical & Physical Properties Molecular Formula C18H24O Exact Mass 256.182709 PSA 20.23000 Index of Refraction 1.555 InChIKey LFYJSSARVMHQJB-QIXNEVBVSA-N |
| Tax Rebate | 9.0% |
| Supervision | None MFN tariff: 5.5% Ordinary tariff: 30.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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