Bakuchiol: Difference between revisions

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| verifiedrevid = 459514403

| ImageSize = 250

| PIN = 4-[(1''E'',3''S'')-3-Ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol

| OtherNames = (+)-Bakuchiol<!-- <br /> -->

| SystematicName =

| Section1 = {{Chembox Identifiers

| CASNo = 10309-37-2

| CASNo_Ref = {{cascite|correct|CAS}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| DrugBank = DB16102

| EC_number = 685-515-4

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| SMILES = Oc1ccc(/C=C/[C@@](\C=C)(C)CC\C=C(/C)C)cc1

| InChI = 1/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

| InChIKey = LFYJSSARVMHQJB-QIXNEVBVBX

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| MeSHName =

| Section2 = {{Chembox Properties

| Formula = C₁₈H₂₄O

| Appearance =

| Density =

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| BoilingPt =

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'''Bakuchiol''' is a [[meroterpenoid]] (a chemical compound having a partial terpenoid structure) in the class terpenophenol.<ref>{{cite book|author1=J. Elks|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA120|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|author2=C. R. Ganellin|date=1990|publisher=Springer|isbn=978-1-4757-2085-3|pages=120–}}</ref>

It was first isolated in 1966 by Mehta et al. from ''[[Psoralea corylifolia]]'' seed and was called Bakuchiol based on the [[Sanskrit]] name of the plant, Bakuchi.<ref>{{Cite journal|last1=Mehta|first1=G.|last2=Nayak|first2=U.Ramdas|last3=Dev|first3=Sukh|date=January 1966|title=Bakuchiol, a novel monoterpenoid|journal=Tetrahedron Letters|volume=7|issue=38|pages=4561–4567|doi=10.1016/s0040-4039(00)70078-5|issn=0040-4039}}</ref> Bakuchiol is a meroterpene phenol abundant in<ref>{{Cite journal|last1=Chaudhuri|first1=R. K.|last2=Bojanowski|first2=K.|title=Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects|url=https://onlinelibrary.wiley.com/doi/10.1111/ics.12117|journal=International Journal of Cosmetic Science|year=2014 |language=en|volume=36|issue=3|pages=221–230|doi=10.1111/ics.12117|pmid=24471735 |s2cid=20823803 |url-access=subscription}}</ref> and mainly obtained from the seeds of the Psoralea corylifolia plant,<ref>{{cite journal |last1=Banerji |first1=A |last2=Chintalwar |first2=G |title=Biosynthesis of bakuchiol, a meroterpene from Psoralea corylifolia |journal=Phytochemistry |volume=22 |issue=9 |year=1983 |pages=1945–1947 |doi=10.1016/0031-9422(83)80019-3|bibcode=1983PChem..22.1945B }} {{INIST|9311490}}</ref><ref name="pmid11731920">{{Cite journal |last1=Cho |first1=Hyun |last2=Jun |first2=Jung-Yang |last3=Song |first3=Eun-Kyoung |last4=Kang |first4=Ki-Hong |last5=Baek |first5=Hum-Young |last6=Ko |first6=Yong-Suk |last7=Kim |first7=Youn-Chul |display-authors=3 |title=Bakuchiol: a hepatoprotective compound of Psoralea corylifolia on tacrine-induced cytotoxicity in Hep G2 cells |journal=Planta Medica |volume=67 |issue=8 |pages=750–751 |date=2001 |doi=10.1055/s-2001-18347 |pmid=11731920 |s2cid=260279217 }}</ref><ref>{{cite journal |author=Manohar, B. |author2=Divakar, S. |author3=Udaya Sankar, K |title=Amyloglucosidase Catalyzed Syntheses of Bakuchiol Glycosides in Supercritical Carbon Dioxide |journal=Bulletin of the Korean Chemical Society |volume=30 |issue=8 |year=2009 |pages=1760–1766 |doi=10.5012/bkcs.2009.30.8.1760|doi-access=free }} {{INIST|22343814}}</ref> which is widely used in Indian [[Ayurveda]]<ref>[https://www.health.harvard.edu/staying-healthy/bakuchiol-does-it-make-skin-look-younger|Bakuchiol: Does it make skin look younger?]</ref> as well as in [[Traditional Chinese medicine]]<ref>{{Cite web|title=Natural Ingredients - Organic Vegan Non-GMO - Grown Sustainably|url=https://theplantmother.com/ingredients/|access-date=2021-12-22|website=Plant Mother|language=en-US}}</ref> to treat a variety of diseases.<ref>{{cite journal |pmid=30521980|year=2019 |last1=Koul |first1=B. |last2=Taak |first2=P. |last3=Kumar |first3=A. |last4=Kumar |first4=A. |last5=Sanyal |first5=I. |title=Genus Psoralea: A review of the traditional and modern uses, phytochemistry and pharmacology |journal=Journal of Ethnopharmacology |volume=232 |pages=201–226 |doi=10.1016/j.jep.2018.11.036 |pmc=7127090 }}</ref> It has also been isolated from other plants, such as P. grandulosa,<ref>{{Cite journal|last1=Labbé|first1=Cecilia|last2=Faini|first2=Francesca|last3=Coll|first3=Joseph|last4=Connolly|first4=Joseph D.|date=July 1996|title=Bakuchiol derivatives from the leaves of Psoralea glandulosa|journal=Phytochemistry|volume=42|issue=5|pages=1299–1303|doi=10.1016/0031-9422(96)00144-6|bibcode=1996PChem..42.1299L |issn=0031-9422}}</ref><ref>{{Cite journal|last1=Nadine Backhouse|first1=C|last2=Delporte|first2=Carla L|last3=Negrete|first3=Rosa E|last4=Erazo|first4=Silvia|last5=Zuñiga|first5=Alexandra|last6=Pinto|first6=Alvaro|last7=Cassels|first7=Bruce K|date=November 2001|title=Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities|journal=Journal of Ethnopharmacology|volume=78|issue=1|pages=27–31|doi=10.1016/s0378-8741(01)00309-9|pmid=11585684|issn=0378-8741}}</ref> P. drupaceae,<ref>{{Cite journal|last1=Lystvan|first1=Kateryna|last2=Belokurova|first2=Valeria|last3=Sheludko|first3=Yuriy|last4=Ingham|first4=John L.|last5=Prykhodko|first5=Valeria|last6=Kishchenko|first6=Olena|last7=Paton|first7=Evgenija|last8=Kuchuk|first8=Mykola|date=2009-12-20|title=Production of bakuchiol by in vitro systems of Psoralea drupacea Bge|journal=Plant Cell, Tissue and Organ Culture|volume=101|issue=1|pages=99–103|doi=10.1007/s11240-009-9657-0|s2cid=10481048|issn=0167-6857}}</ref> [[Ulmus davidiana]],<ref>{{Cite journal|last1=Choi|first1=Sang Yoon|last2=Lee|first2=Sanghyun|last3=Choi|first3=Won-Hee|last4=Lee|first4=Yeonmi|last5=Jo|first5=Youn Ock|last6=Ha|first6=Tae-Youl|date=August 2010|title=Isolation and Anti-Inflammatory Activity of Bakuchiol from Ulmus davidiana var. japonica|journal=Journal of Medicinal Food|volume=13|issue=4|pages=1019–1023|doi=10.1089/jmf.2009.1207|pmid=20553183|issn=1096-620X}}</ref> [[Otholobium pubescens]],<ref>{{cite journal |last1=Krenisky |first1=Joann M. |last2=Luo |first2=Jian |last3=Reed |first3=Michael J. |last4=Carney |first4=John R. |display-authors=3 |title=Isolation and Antihyperglycemic Activity of Bakuchiol from Otholobium pubescens (Fabaceae), a Peruvian Medicinal Plant Used for the Treatment of Diabetes. |journal=Biological & Pharmaceutical Bulletin |volume=22 |issue=10 |year=1999 |pages=1137–1140 |pmid=10549873 |doi=10.1248/bpb.22.1137 |doi-access=free }} {{INIST|1198639}}</ref> [[Long pepper|Piper longum]]<ref>{{Cite journal|last1=Ohno|first1=Osamu|last2=Watabe|first2=Taeko|last3=Nakamura|first3=Kazuhiko|last4=Kawagoshi|first4=Masaru|last5=Uotsu|first5=Nobuo|last6=Chiba|first6=Tomohiro|last7=Yamada|first7=Masayoshi|last8=Yamaguchi|first8=Kohji|last9=Yamada|first9=Kaoru|date=2010-07-23|title=Inhibitory Effects of Bakuchiol, Bavachin, and Isobavachalcone Isolated from Piper longumon Melanin Production in B16 Mouse Melanoma Cells|journal=Bioscience, Biotechnology, and Biochemistry|volume=74|issue=7|pages=1504–1506|doi=10.1271/bbb.100221|pmid=20622433|s2cid=12449051|issn=0916-8451}}</ref> and Aerva sangulnolenta Blum.<ref>{{Citation|chapter=Aerva Sanguinolenta (L.) Blume, Extract 116425-35-5|date=2012-10-15|publisher=John Wiley & Sons, Inc.|isbn=978-0-471-70134-7|doi=10.1002/0471701343.sdp26534|title=Sax's Dangerous Properties of Industrial Materials|pages=1–2 }}</ref>

Even though the first complete synthesis of Bakuchiol was described in 1973,<ref>{{Cite journal|last1=Damodaran|first1=N.P.|last2=Dev|first2=Sukh|date=January 1973|title=Meroterpenoids—III|journal=Tetrahedron|volume=29|issue=9|pages=1209–1213|doi=10.1016/0040-4020(73)80103-6|issn=0040-4020}}</ref> its first commercial use in topical applications did not occur until 2007 when it was introduced to the market under the trade name Sytenol A by Sytheon Ltd.<ref>{{Citation|last=Chaudhuri|first=Ratan|title=Bakuchiol: A Retinol-Like Functional Compound, Modulating Multiple Retinol and Non-Retinol Targets|date=2015-09-18|url=http://www.crcnetbase.com/doi/10.1201/b18895-2|work=Cosmeceuticals and Active Cosmetics, Third Edition|pages=1–18|editor-last=Sivamani|editor-first=Raja|publisher=CRC Press|language=en|doi=10.1201/b18895-2|isbn=978-1-4822-1416-1|access-date=2019-08-02|editor2-last=Jagdeo|editor2-first=Jared|editor3-last=Elsner|editor3-first=Peter|editor4-last=Maibach|editor4-first=Howard}}{{Dead link|date=September 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

It has been reported to have anticancer activity in [[preclinical model]]s, possibly due to its structural similarity with [[resveratrol]].<ref>{{cite journal |last1=Chen |first1=Zhe |last2=Jin |first2=Ke |last3=Gao |first3=Lingyan |last4=Lou |first4=Guodong |last5=Jin |first5=Ying |last6=Yu |first6=Yongping |last7=Lou |first7=Yijia |display-authors=3 |title=Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line |journal=European Journal of Pharmacology |volume=643 |issue=2–3 |year=2010 |pages=170–9 |pmid=20599920 |doi=10.1016/j.ejphar.2010.06.025}}</ref> One study in rats suggested that Bakuchiol and ethanol extracts of the Chinese medicinal plant ''Psoralea corylifolia'' could protect against [[Osteoporosis|bone loss]].<ref>{{cite journal |last1=Lim |first1=Sun-Hye |last2=Ha |first2=Tae-Youl |last3=Kim |first3=Sung-Ran |last4=Ahn |first4=Jiyun |last5=Park |first5=Hyun Jin |last6=Kim |first6=Suna |display-authors=3 |title=Ethanol extract of Psoralea corylifolia L. and its main constituent, bakuchiol, reduce bone loss in ovariectomised Sprague–Dawley rats |journal=British Journal of Nutrition |volume=101 |issue=7 |year=2008 |pages=1031–1039 |pmid=18801207 |doi=10.1017/S0007114508066750|doi-access=free }}</ref>

Bakuchiol possesses antioxidant,<ref>{{Cite journal|last1=Adhikari|first1=S.|last2=Joshi|first2=R.|last3=Patro|first3=B. S.|last4=Ghanty|first4=T. K.|last5=Chintalwar|first5=G. J.|last6=Sharma|first6=A.|last7=Chattopadhyay|first7=S.|last8=Mukherjee|first8=T.|date=September 2003|title=Antioxidant Activity of Bakuchiol: Experimental Evidences and Theoretical Treatments on the Possible Involvement of the Terpenoid Chain|journal=Chemical Research in Toxicology|volume=16|issue=9|pages=1062–1069|doi=10.1021/tx034082r|pmid=12971793|issn=0893-228X}}</ref><ref>{{Cite journal|last1=Haraguchi|first1=Hiroyuki|last2=Inoue|first2=Junji|last3=Tamura|first3=Yukiyoshi|last4=Mizutani|first4=Kenji|date=2002|title=Antioxidative components of Psoralea corylifolia (Leguminosae)|journal=Phytotherapy Research|volume=16|issue=6|pages=539–544|doi=10.1002/ptr.972|pmid=12237811|s2cid=27269600|issn=0951-418X}}</ref> anti-inflammatory,<ref>{{Cite journal|last1=Ferrándiz|first1=María Luisa|last2=Gil|first2=Blanca|last3=Sanz|first3=María Jesús|last4=Ubeda|first4=Amalia|last5=Erazo|first5=Silvia|last6=González|first6=Ernesto|last7=Negrete|first7=Rosa|last8=Pacheco|first8=Sergio|last9=Payáa|first9=Miguel|date=September 1996|title=Effect of Bakuchiol on Leukocyte Functions and Some Inflammatory Responses in Mice|journal=Journal of Pharmacy and Pharmacology|volume=48|issue=9|pages=975–980|doi=10.1111/j.2042-7158.1996.tb06016.x|pmid=8910867|s2cid=25409612|issn=0022-3573}}</ref><ref>{{Cite journal|last1=Nadine Backhouse|first1=C|last2=Delporte|first2=Carla L|last3=Negrete|first3=Rosa E|last4=Erazo|first4=Silvia|last5=Zuñiga|first5=Alexandra|last6=Pinto|first6=Alvaro|last7=Cassels|first7=Bruce K|date=November 2001|title=Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities|journal=Journal of Ethnopharmacology|volume=78|issue=1|pages=27–31|doi=10.1016/s0378-8741(01)00309-9|pmid=11585684|issn=0378-8741}}</ref> and antibacterial<ref>{{Cite journal|last1=Katsura|first1=H.|last2=Tsukiyama|first2=R.-I.|last3=Suzuki|first3=A.|last4=Kobayashi|first4=M.|date=2001-11-01|title=In Vitro Antimicrobial Activities of Bakuchiol against Oral Microorganisms|journal=Antimicrobial Agents and Chemotherapy|volume=45|issue=11|pages=3009–3013|doi=10.1128/aac.45.11.3009-3013.2001|pmid=11600349|issn=0066-4804|pmc=90775}}</ref> properties. 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.<ref>{{cite journal |author=Parimala Devi B, Ramasubramaniaraj R |date=2009 |title=Dental Caries and Medicinal Plants – An Overview |url=http://jprsolutions.info/article_detail.php?article_id=632 |journal=Journal of Pharmacy Research |volume=2 |issue=11 |pages=1669–1675 }}</ref>

Despite having no structural resemblance to [[retinol]],<ref>{{Cite journal|last1=Dhaliwal|first1=S.|last2=Rybak|first2=I.|last3=Ellis|first3=S.R.|last4=Notay|first4=M.|last5=Trivedi|first5=M.|last6=Burney|first6=W.|last7=Vaughn|first7=A.R.|last8=Nguyen|first8=M.|last9=Reiter|first9=P.|last10=Bosanac|first10=S.|last11=Yan|first11=H.|title=Prospective, randomized, double-blind assessment of topical bakuchiol and retinol for facial photoageing|journal=British Journal of Dermatology|year=2019 |language=en|volume=180|issue=2|pages=289–296|doi=10.1111/bjd.16918|pmid=29947134 |s2cid=49430951 |issn=0007-0963|doi-access=free|hdl=2027.42/147746|hdl-access=free}}</ref> Bakuchiol was found to have retinol functionality through retinol-like regulation of gene expression.<ref name="pmid24471735">{{Cite journal |author=Chaudhuri RK, Bojanowski K |title=Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects |journal=International Journal of Cosmetic Science |volume=36 |issue=3 |pages=221–230 |date=2014 |pmid=24471735 |doi=10.1111/ics.12117 |s2cid=20823803 }}</ref><ref>{{Cite journal|last1=Chaudhuri|first1=R. K.|last2=Bojanowski|first2=K.|title=Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects|url=https://onlinelibrary.wiley.com/doi/10.1111/ics.12117|journal=International Journal of Cosmetic Science|year=2014 |language=en|volume=36|issue=3|pages=221–230|doi=10.1111/ics.12117|pmid=24471735 |s2cid=20823803 |url-access=subscription}}</ref> In 2018, a randomized, [[Blinded experiment|double-blind]], 12-week clinical study with 44 volunteers demonstrated that Bakuchiol is comparable with retinol in its ability to improve photoaging (wrinkles, hyperpigmentation) but has a better skin tolerance.<ref>{{Cite journal|last1=Dhaliwal|first1=S.|last2=Rybak|first2=I.|last3=Ellis|first3=S.R.|last4=Notay|first4=M.|last5=Trivedi|first5=M.|last6=Burney|first6=W.|last7=Vaughn|first7=A.R.|last8=Nguyen|first8=M.|last9=Reiter|first9=P.|date=February 2019|title=Prospective, randomized, double-blind assessment of topical bakuchiol and retinol for facial photoageing|journal=British Journal of Dermatology|volume=180|issue=2|pages=289–296|doi=10.1111/bjd.16918|pmid=29947134|issn=0007-0963|doi-access=free|hdl=2027.42/147746|hdl-access=free}}</ref>

Bakuchiol has been found to possess [[antiandrogen]]ic activity in prostate [[cancer cell]]s, which inhibited [[cell proliferation]].<ref name="MiaoMa2013">{{cite journal |author=Miao L. |author2=Ma S |author3=Fan G |display-authors=etal|date=2013 |title=Bakuchiol inhibits the androgen induced-proliferation of prostate cancer cell line LNCaP through suppression of AR transcription activity |journal=Tianjin Journal of Traditional Chinese Medicine |volume=30 |issue=5 |pages=291–293 |doi=10.11656/j.issn.1672-1519.2013.05.13 |doi-broken-date=2024-02-19 }} original title: 补骨脂酚拮抗AR转录活性抑制雄激素诱导的前列腺癌细胞LNCaP的增殖</ref>

==See also==

* [[Drupanol]]

{{Reflist|2}}

* [https://krasotashop.com/blog/chto-takoe-bakuchiol-i-naskolko-on-effektiven.html what bacuchiol is and how effective it is]

{{Androgen receptor modulators}}

[[Category:Nonsteroidal antiandrogens]]

[[Category:Terpeno-phenolic compounds]]