Bakuchiol | CAS#10309-37-2 | antimicrobial | PP1B inhibitor

MedKoo Cat#: 540040 | Name: Bakuchiol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bakuchiol is an ERα agonist found in various plant sources. It exhibits a wide variety of applications, such as an antimicrobial, suppression of LPS-stimulated production of pro-inflammatory cytokines, decreasing plasma glucose and triglyceride levels, and potentially inhibiting PP1B.

Chemical Structure

Bakuchiol

CAS#10309-37-2

Theoretical Analysis

MedKoo Cat#: 540040

Name: Bakuchiol

CAS#: 10309-37-2

Chemical Formula: C18H24O

Exact Mass: 256.1827

Molecular Weight: 256.38

Elemental Analysis: C, 84.32; H, 9.44; O, 6.24

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
250mg	USD 650.00	2 Weeks
1g	USD 1,250.00	2 Weeks

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Related CAS #

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Synonym

Bakuchiol; Drupanol; Chiba; NSC-671195; NSC671195; NSC 671195; UP-256; UP256; UP-256; W1975; W 1975; W-1975

IUPAC/Chemical Name

(E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenol

InChi Key

LFYJSSARVMHQJB-WYMLVPIESA-N

InChi Code

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+

SMILES Code

OC1=CC=C(/C=C/C(C)(C=C)CC/C=C(C)\C)C=C1

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bakuchiol is an ERα agonist.

In vitro activity:

To determine the effects of bakuchiol on the production of PGE2 and the inflammatory cytokines IL-6 and TNF-α after LPS (lipopolysaccharide) stimulation, BV-2 cells were pretreated with various concentrations of bakuchiol (0, 1.25, 2.5, or 5 μM) for 2 h and then stimulated with LPS (1 μg/mL) for an additional 22 h. As shown in Figure 1D, LPS treatment significantly increased PGE2 production compared with untreated cells. In contrast, bakuchiol significantly inhibited the PGE2 production induced by LPS stimulation. The production of TNF-α and IL-6 was significantly increased in LPS-stimulated BV-2 cells compared with untreated cells. Bakuchiol significantly decreased the production of IL-6 in a dose-dependent manner, but LPS-stimulated TNF-α production was not affected in BV-2 cells (Figure 1E,F). Reference: Int J Mol Sci. 2019 Jul 22;20(14):3574. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6678636/

In vivo activity:

LPS treatment in a murine model of inflammation was used to study the suppressive effects of bakuchiol on neuroinflammation in vivo. Microglial cells were immunostained with the Iba-1. LPS-treated mice demonstrated increased expression of Iba-1 compared to vehicle-treated controls; however, expression of Iba-1 were decreased in bakuchiol-treated mice (Figure 5B). In addition, as shown in Figure 5C,D, production of TNF-α and IL-6 in the serum were significantly increased in LPS-treated mice compared to vehicle-treated control mice. Reference: Int J Mol Sci. 2019 Jul 22;20(14):3574. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6678636/

	Solvent	mg/mL	mM
Solubility
	DMSO	62.5	243.78

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 256.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Lim HS, Kim YJ, Kim BY, Jeong SJ. Bakuchiol Suppresses Inflammatory Responses Via the Downregulation of the p38 MAPK/ERK Signaling Pathway. Int J Mol Sci. 2019 Jul 22;20(14):3574. doi: 10.3390/ijms20143574. PMID: 31336605; PMCID: PMC6678636.

In vitro protocol:

In vivo protocol:

1: Shoji M, Arakaki Y, Esumi T, Kohnomi S, Yamamoto C, Suzuki Y, Takahashi E, Konishi S, Kido H, Kuzuhara T. Bakuchiol Is a Phenolic Isoprenoid with Novel Enantiomer-selective Anti-influenza A Virus Activity Involving Nrf2 Activation. J Biol Chem. 2015 Nov 13;290(46):28001-17. doi: 10.1074/jbc.M115.669465. Epub 2015 Oct 7. PubMed PMID: 26446794; PubMed Central PMCID: PMC4646038. 2: Mao H, Wang H, Ma S, Xu Y, Zhang H, Wang Y, Niu Z, Fan G, Zhu Y, Gao XM. Bidirectional regulation of bakuchiol, an estrogenic-like compound, on catecholamine secretion. Toxicol Appl Pharmacol. 2014 Jan 1;274(1):180-9. doi: 10.1016/j.taap.2013.11.001. Epub 2013 Nov 11. PubMed PMID: 24231057. 3: Dong DG, Zhang Y, Zhang SL, Lv J, Guo EM, Fang ZZ, Cao YF. Inhibition potential of UDP-glucuronosyltransferases (Ugts) 1A isoforms by the analogue of resveratrol, bakuchiol. Pharmazie. 2014 Jan;69(1):60-3. PubMed PMID: 24601226. 4: Park MH, Kim JH, Chung YH, Lee SH. Bakuchiol sensitizes cancer cells to TRAIL through ROS- and JNK-mediated upregulation of death receptors and downregulation of survival proteins. Biochem Biophys Res Commun. 2016 Apr 29;473(2):586-92. doi: 10.1016/j.bbrc.2016.03.127. Epub 2016 Mar 28. PubMed PMID: 27033605. 5: Hu C, Liang Q, Tang X, Wang Y, Ma Z, Xiao C, Tan H, Gao Y, Huang X. In vivo metabolite identification of bakuchiol in rats by UPLC/ESI-PDA-QTOF-MS. Fitoterapia. 2015 Oct;106:129-34. doi: 10.1016/j.fitote.2015.09.005. Epub 2015 Sep 5. PubMed PMID: 26347955. 6: Nordin MA, Abdul Razak F, Himratul-Aznita WH. Assessment of Antifungal Activity of Bakuchiol on Oral-Associated Candida spp. Evid Based Complement Alternat Med. 2015;2015:918624. doi: 10.1155/2015/918624. Epub 2015 Nov 8. PubMed PMID: 26633986; PubMed Central PMCID: PMC4655055. 7: Kim JE, Kim JH, Lee Y, Yang H, Heo YS, Bode AM, Lee KW, Dong Z. Bakuchiol suppresses proliferation of skin cancer cells by directly targeting Hck, Blk, and p38 MAP kinase. Oncotarget. 2016 Mar 22;7(12):14616-27. doi: 10.18632/oncotarget.7524. PubMed PMID: 26910280; PubMed Central PMCID: PMC4924739. 8: Yu Q, Zou HM, Wang S, Xu YM, Li JM, Zhang N. [Regulative effect of bakuchiol on ESF-1 cells anti-aging gene]. Zhong Yao Cai. 2014 Apr;37(4):632-5. Chinese. PubMed PMID: 25345139. 9: Lau KM, Wong JH, Wu YO, Cheng L, Wong CW, To MH, Lau CP, Yew DT, Leung PC, Fung KP, Hui M, Ng TB, Lau CB. 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. doi: 10.1016/j.phymed.2014.03.005. Epub 2014 Apr 2. PubMed PMID: 24703327. 10: Chi M, Peng Y, Zheng J. Characterization of glutathione conjugates derived from reactive metabolites of bakuchiol. Chem Biol Interact. 2016 Jan 25;244:178-86. doi: 10.1016/j.cbi.2015.12.009. Epub 2015 Dec 19. PubMed PMID: 26712081. 11: Chaudhuri RK, Bojanowski K. Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects. Int J Cosmet Sci. 2014 Jun;36(3):221-30. doi: 10.1111/ics.12117. Epub 2014 Mar 6. PubMed PMID: 24471735. 12: Zhang SQ, Fan YM. Ultra-high-performance liquid chromatography-tandem mass spectrometry for pharmacokinetics of bakuchiol in rats. Biomed Chromatogr. 2014 Mar;28(3):433-8. doi: 10.1002/bmc.3051. Epub 2013 Sep 23. PubMed PMID: 24115152. 13: Lee SJ, Yoo M, Go GY, Kim DH, Choi H, Leem YE, Kim YK, Seo DW, Ryu JH, Kang JS, Bae GU. Bakuchiol augments MyoD activation leading to enhanced myoblast differentiation. Chem Biol Interact. 2016 Mar 25;248:60-7. doi: 10.1016/j.cbi.2016.02.008. Epub 2016 Feb 18. PubMed PMID: 26902638. 14: Zhao ZJ, Gong Z, Shi SZ, Yang JL, Ma NN, Wang Q. [Toxicokinetics of bakuchiol, hepatic and renal toxicity in rats after single oral administration of Psoraleae Fructus and combination with Glycyrrhizae Radix et Rhizoma]. Zhongguo Zhong Yao Za Zhi. 2015 Jun;40(11):2221-6. Chinese. PubMed PMID: 26552185. 15: Jeong M, Hong T, Lee K, Hwangbo H, Kim M, Ma W, Zahn M. HPLC Method for Simultaneous Quantification of Bakuchiol and Minor Furocoumarins in Bakuchiol Extract from Psoralea corylifolia. J AOAC Int. 2015 Jul-Aug;98(4):902-6. doi: 10.5740/jaoacint.14-228. PubMed PMID: 26268970. 16: Xu Y, Li P, Zhang X, Wang J, Gu D, Wang Y. 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. doi: 10.4314/ahs.v14i3.10. PubMed PMID: 25352873; PubMed Central PMCID: PMC4209642. 17: Li L, Chen X, Liu CC, Lee LS, Man C, Cheng SH. Phytoestrogen Bakuchiol Exhibits In Vitro and In Vivo Anti-breast Cancer Effects by Inducing S Phase Arrest and Apoptosis. Front Pharmacol. 2016 May 24;7:128. doi: 10.3389/fphar.2016.00128. eCollection 2016. PubMed PMID: 27252650; PubMed Central PMCID: PMC4877368. 18: Wang PL, Zhang FX, Qiu ZC, Yao ZH, Wong MS, Yao XS, Dai Y. Isolation and identification of metabolites of bakuchiol in rats. Fitoterapia. 2016 Mar;109:31-8. doi: 10.1016/j.fitote.2015.11.006. Epub 2015 Nov 14. PubMed PMID: 26586623. 19: Zhuang X, Zhong Y, Yuan M, Li H. Pre-column derivatization combined with UHPLC-MS/MS for rapid and sensitive quantification of bakuchiol in rat plasma. J Pharm Biomed Anal. 2013 Mar 5;75:18-24. doi: 10.1016/j.jpba.2012.11.001. Epub 2012 Nov 10. PubMed PMID: 23312380. 20: Lin J, Yao HJ, Li RY. Bakuchiol inhibits cell proliferation and induces apoptosis and cell cycle arrest in SGC-7901 human gastric cancer cells. J BUON. 2016 Jul-Aug;21(4):889-894. PubMed PMID: 27685910.