bakuchiol
4-[(1E,3S)-3,7-dimethyl-3-vinyl-1,6-octadien-1-yl]phenol
Identification
| Name | bakuchiol |
| IUPAC | 4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol |
| CAS Number | 10309-37-2 |
| FDA UNII | OT12HJU3AR |
| Molecular Formula | C18 H24 O |
| Molecular Weight | 256.38848000 |
| MDL Number | MFCD01707441 |
| Nikkaji Number | J15.045B |
| Beilstein | 3611720 |
Regulatory
Physical Properties
| Appearance | yellow red clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 391.40 °C. @ 760.00 mm Hg (est) |
| Flash Point | 350.00 °F. TCC ( 176.60 °C. ) (est) |
| logP (o/w) | 6.400 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 94 mg/kg |
| Dermal Toxicity | subcutaneous-rat LD > 1000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for bakuchiol usage levels up to | not for fragrance use. |
| Recommendation for bakuchiol flavor usage levels up to | not for flavor use. |
BOC Sciences
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Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...
O'Laughlin Industries Inc.
Manufacturer of chemicals and ingredients used in flavors, fragrances, food, beverages and cosmetics
Leading the Flavor and Fragrance Industry since 1980.
Potential Uses
Natural Occurrence
Synonyms
backuchiol
(+)-
bakuchiol
(S)-
bakuchiol
4-[(1E,3S)-3,7-
dimethyl-3-vinyl-1,6-octadien-1-yl]phenol
4-[(1E,3S)-3,7-
dimethyl-3-vinylocta-1,6-dien-1-yl]phenol
(S)-4-(3,7-
dimethyl-3-vinylocta-1,6-dienyl)phenol
4-((1E)(3S)-3,7-
dimethyl-3-vinylocta-1,6-dienyl)phenol
drupanol
4-(3-
ethenyl-3,7-dimethyl-1,6-octadienyl) phenol
4-[(1E,3S)-3-
ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol
4-[(1E,3S)-3-
ethenyl-3,7-dimethylocta-1,6-dienyl]phenol
phenol, 4-(3-ethenyl-3,7-dimethyl-1,6-octadienyl)-, (S-(E))-
phenol, 4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadien-1-yl]-
phenol, 4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadienyl]-
PubMed:
Bakuchiol Is a Phenolic Isoprenoid with Novel Enantiomer-selective Anti-influenza A Virus Activity Involving Nrf2 Activation.
PubMed:
In vivo metabolite identification of bakuchiol in rats by UPLC/ESI-PDA-QTOF-MS.
PubMed:
HPLC Method for Simultaneous Quantification of Bakuchiol and Minor Furocoumarins in Bakuchiol Extract from Psoralea corylifolia.
PubMed:
Anti-dermatophytic activity of bakuchiol: in vitro mechanistic studies and in vivo tinea pedis-inhibiting activity in a guinea pig model.
PubMed:
Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects.
PubMed:
Ultra-high-performance liquid chromatography-tandem mass spectrometry for pharmacokinetics of bakuchiol in rats.
PubMed:
Bidirectional regulation of bakuchiol, an estrogenic-like compound, on catecholamine secretion.
PubMed:
[Toxicokinetics of bakuchiol, hepatic and renal toxicity in rats after single oral administration of Psoraleae Fructus and combination with Glycyrrhizae Radix et Rhizoma].
PubMed:
Inhibition potential of UDP-glucuronosyltransferases (Ugts) 1A isoforms by the analogue of resveratrol, bakuchiol.
PubMed:
[Regulative effect of bakuchiol on ESF-1 cells anti-aging gene].
PubMed:
A dermocosmetic containing bakuchiol, Ginkgo biloba extract and mannitol improves the efficacy of adapalene in patients with acne vulgaris: result from a controlled randomized trial.
PubMed:
[Metabolic detoxification of bakuchiol is mediated by cytochrome P450 enzymes in human liver microsomes].
PubMed:
Pre-column derivatization combined with UHPLC-MS/MS for rapid and sensitive quantification of bakuchiol in rat plasma.
PubMed:
Self-micro emulsifying formulation improved intestinal absorption and oral bioavailability of bakuchiol.
PubMed:
Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated Claisen rearrangement and total synthesis of (+)-bakuchiol.
PubMed:
Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line.
PubMed:
Bakuchiol derivatives as novel and potent cytotoxic agents: a report.
PubMed:
Positive skeletal effect of two ingredients of Psoralea corylifolia L. on estrogen deficiency-induced osteoporosis and the possible mechanisms of action.
PubMed:
In vivo pharmacokinetics of bakuchiol after oral administration of bakuchiol extraction in rat plasma.
PubMed:
Antiphytopathogenic activity of Psoralea glandulosa (Fabaceae) against Botrytis cinerea and Phytophthora cinnamomi.
PubMed:
Protective effects of the compounds isolated from the seed of Psoralea corylifolia on oxidative stress-induced retinal damage.
PubMed:
In vitro evidence for bakuchiol's influence towards drug metabolism through inhibition of UDP-glucuronosyltransferase (UGT) 2B7.
PubMed:
Novel bisstyryl derivatives of bakuchiol: targeting oral cavity pathogens.
PubMed:
Isolation and anti-inflammatory activity of Bakuchiol from Ulmus davidiana var. japonica.
PubMed:
[Vitro antitumor activity and synthesis of the key intermediate of bakuchiol].
PubMed:
Psoralea glandulosa as a potential source of anticancer agents for melanoma treatment.
PubMed:
Ethanol extract of Psoralea corylifolia L. and its main constituent, bakuchiol, reduce bone loss in ovariectomised Sprague-Dawley rats.
PubMed:
Inhibitory effects of bakuchiol, bavachin, and isobavachalcone isolated from Piper longum on melanin production in B16 mouse melanoma cells.
PubMed:
Bakuchiol-induced caspase-3-dependent apoptosis occurs through c-Jun NH2-terminal kinase-mediated mitochondrial translocation of Bax in rat liver myofibroblasts.
PubMed:
Protective effect of (S)-bakuchiol from Psoralea corylifolia on rat liver injury in vitro and in vivo.
PubMed:
In vitro antimicrobial activities of bakuchiol against oral microorganisms.
PubMed:
Preparation and in vitro evaluation of radioiodinated bakuchiol as an anti tumor agent.
PubMed:
Effect of bakuchiol on leukocyte functions and some inflammatory responses in mice.
PubMed:
[Cytotoxicity of corylifoliae fructus. II. Cytotoxicity of bakuchiol and the analogues].
PubMed:
Enantioselective synthesis of Bakuchiol using diazosulfonate C-H insertion to install the quaternary center.
PubMed:
Bakuchiol, an antibacterial component of Psoralidium tenuiflorum.
PubMed:
Meroterpenes from Psoralea corylifolia against Pyricularia oryzae.
PubMed:
Bakuchiol analogs inhibit monoamine transporters and regulate monoaminergic functions.
PubMed:
Inhibition of mitochondrial lipid peroxidation by Bakuchiol, a meroterpene from Psoralea corylifolia.
PubMed:
Antioxidant activity of bakuchiol: experimental evidences and theoretical treatments on the possible involvement of the terpenoid chain.
PubMed:
[Determination of bakuchiol in the fruit of Psoralea corylifolia L].
PubMed:
Estrogenic activities of Psoralea corylifolia L. seed extracts and main constituents.
PubMed:
Fructus Psoraleae contains natural compounds with potent inhibitory effects towards human carboxylesterase 2.
PubMed:
Isolation and antihyperglycemic activity of bakuchiol from Otholobium pubescens (Fabaceae), a Peruvian medicinal plant used for the treatment of diabetes.
PubMed:
Fate of leucine in the biosynthesis of bakuchiol, a meroterpene from Psoralea corylifolia.
PubMed:
Synthesis and structure-immunosuppressive activity relationships of bakuchiol and its derivatives.
PubMed:
Bakuchiol: a hepatoprotective compound of Psoralea corylifolia on tacrine-induced cytotoxicity in Hep G2 cells.
PubMed:
[A study on toxicity of bakuchiol to mice's kidney (author's transl)].
PubMed:
Hypoxia-inducible factor-1 and nuclear factor-kappaB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia.
PubMed:
Bakuchiol from Psoralea corylifolia inhibits the expression of inducible nitric oxide synthase gene via the inactivation of nuclear transcription factor-kappaB in RAW 264.7 macrophages.
PubMed:
[The effect of bakuchiol on the ultra-thin layer structure of Staphylococcus aureus 209 cells].
PubMed:
[Antimicrobial activity and toxicity of the antibiotic, bakuchiol].
PubMed:
Prediction of Drug-Induced Liver Injury in HepG2 Cells Cultured with Human Liver Microsomes.
PubMed:
[Kinetics of the anti-staphylococcal activity of bakuchiol in vitro (author's transl)].
PubMed:
Cyclobakuchiol C, a new bakuchiol derivative from Psoralea coryllfolia.
PubMed:
[Antimicrobial properties of bakuchiol in in vitro experiments].
PubMed:
Psoralea corylifolia L. (Buguchi) - folklore to modern evidence: review.
PubMed:
Antifungal study of the resinous exudate and of meroterpenoids isolated from Psoralea glandulosa (Fabaceae).
PubMed:
Antifolate Activity of Plant Polyphenols against Mycobacterium tuberculosis.
PubMed:
Constituents of Psoralea corylifolia Fruits and Their Effects on Methicillin-Resistant Staphylococcus aureus.
PubMed:
Phenolic compounds isolated from Psoralea corylifolia inhibit IL-6-induced STAT3 activation.
PubMed:
Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro.
PubMed:
[Constituent of natural food additive hokosshi extract and an analytical method for the additive in foods].
PubMed:
Psoralea corylifolia L. seed extract ameliorates streptozotocin-induced diabetes in mice by inhibition of oxidative stress.
PubMed:
Osteoblasts proliferation and differentiation stimulating activities of the main components of Fructus Psoraleae corylifoliae.
PubMed:
Tumor cell death induced by the inhibition of mitochondrial electron transport: the effect of 3-hydroxybakuchiol.
PubMed:
Protective Role of Psoralea corylifolia L. Seed Extract against Hepatic Mitochondrial Dysfunction Induced by Oxidative Stress or Aging.
PubMed:
Studies on lymphangiogenesis inhibitors from Korean and Japanese crude drugs.
PubMed:
Antioxidative components of Psoralea corylifolia (Leguminosae).
PubMed:
Two antifungal components isolated from Fructus Psoraleae and Folium Eucalypti Globuli by bioassay-guided purification.
PubMed:
[Variation of 4 kinds of compounds in Psoralea corylifolia processed by different methods].
PubMed:
[Comparison of ancient and modern processing methods for fructus Psoraleae].
PubMed:
Synthesis of quaternary carbon stereogenic centers through enantioselective Cu-catalyzed allylic substitutions with vinylaluminum reagents.
PubMed:
[Studies on chemical constituents in rhizome of Elaeagnus bockii I].
PubMed:
DNA polymerase and topoisomerase II inhibitors from Psoralea corylifolia.
PubMed:
Targeting tumor proteasome with traditional Chinese medicine.
PubMed:
Phytoestrogens from Psoralea corylifolia reveal estrogen receptor-subtype selectivity.
PubMed:
Physico-chemical studies on the evaluation of the antioxidant activity of herbal extracts and active principles of some Indian medicinal plants.
PubMed:
Chemical fingerprint and quantitative analysis of fructus psoraleae by high-performance liquid chromatography.
PubMed:
[Cytotoxicity of Corylifoliae fructus. I. Isolation of the effective compound and the cytotoxicity].
PubMed:
Bioactive constituents from Chinese natural medicines. XXXIII. Inhibitors from the seeds of Psoralea corylifolia on production of nitric oxide in lipopolysaccharide-activated macrophages.
PubMed:
The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis.
PubMed:
Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities.
PubMed:
In vitro BACE-1 inhibitory phenolic components from the seeds of Psoralea corylifolia.
PubMed:
In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia.
PubMed:
[The effect of solar ultraviolet on the system of microorganisms-higher plant antibiotics, a natural phenomenon and a new approach to enhancing the efficacy of antibiotics].
PubMed:
Plant antimutagenic agents, 2. Flavonoids.
PubMed:
[Bacuchiol activity against the tobacco mosaic virus].