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10309-37-2,MFCD01707441
Catalog No.:AA0033Q1

10309-37-2 | Bakuchiol

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100mg
96%
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$51.00   $36.00
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250mg
96%
in stock  
$77.00   $54.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0033Q1
Chemical Name:
Bakuchiol
CAS Number:
10309-37-2
Molecular Formula:
C18H24O
Molecular Weight:
256.3826
MDL Number:
MFCD01707441
SMILES:
C=C[C@@](/C=C/c1ccc(cc1)O)(CCC=C(C)C)C
NSC Number:
671195
Properties
Properties
 
BP:
391.4 °C at 760 mmHg  
Form:
Liquid  
Refractive Index:
1.4500 (estimate)  
Storage:
Inert atmosphere;-20 ℃;  

Computed Properties
 
Complexity:
328  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
6  
XLogP3:
6.1  

Downstream Synthesis Route

[1]Locationinpatent:experimentalpartMallepallyV.Reddy;NiranjanThota;PayareL.Sangwan;PankajMalhotra;FurqanAli;InshadA.Khan;SwapandeepS.Chimni;Koul,Surrinder[EuropeanJournalofMedicinalChemistry,2010,vol.45,#7,p.3125-3134]

[2]Locationinpatent:experimentalpartMajeed,Rabiya;Reddy,MallepallyV.;Chinthakindi,PraveenK.;Sangwan,PayareL.;Hamid,Abid;Chashoo,Gousia;Saxena,AjitK.;Koul,Surrinder[EuropeanJournalofMedicinalChemistry,2012,vol.49,p.55-67]

[3]Gautam,LekhNath;Ling,Taotao;Lang,Walter;Rivas,Fatima[EuropeanJournalofMedicinalChemistry,2016,vol.113,p.75-80]

[4]Mehta,G.etal.[Tetrahedron,1973,vol.29,p.1119-1125]

[1]Locationinpatent:experimentalpartMallepallyV.Reddy;NiranjanThota;PayareL.Sangwan;PankajMalhotra;FurqanAli;InshadA.Khan;SwapandeepS.Chimni;Koul,Surrinder[EuropeanJournalofMedicinalChemistry,2010,vol.45,#7,p.3125-3134]

[2]Wu,Cheng-Zhu;Liu,Da-Chuan;Guo,Xing;Dai,Yiqun;Ma,Tao;Li,Hong-Mei;Huo,Qiang[Molecules,2018,vol.23,#3]

[3]Mehta,G.etal.[Tetrahedron,1973,vol.29,p.1119-1125]

[4]Wu,Cheng-Zhu;Hong,SeongSu;Cai,XingFu;Dat,NguyenTien;Nan,Ji-Xing;Hwang,BangYeon;Lee,JungJoon;Lee,Dongho[BioorganicandMedicinalChemistryLetters,2008,vol.18,#8,p.2619-2623]

[1]Locationinpatent:experimentalpartMallepallyV.Reddy;NiranjanThota;PayareL.Sangwan;PankajMalhotra;FurqanAli;InshadA.Khan;SwapandeepS.Chimni;Koul,Surrinder[EuropeanJournalofMedicinalChemistry,2010,vol.45,#7,p.3125-3134]

[2]Gautam,LekhNath;Ling,Taotao;Lang,Walter;Rivas,Fatima[EuropeanJournalofMedicinalChemistry,2016,vol.113,p.75-80]

[3]Locationinpatent:experimentalpartMajeed,Rabiya;Reddy,MallepallyV.;Chinthakindi,PraveenK.;Sangwan,PayareL.;Hamid,Abid;Chashoo,Gousia;Saxena,AjitK.;Koul,Surrinder[EuropeanJournalofMedicinalChemistry,2012,vol.49,p.55-67]

[4]Chen,Hongli;Du,Xiaolong;Tang,Wei;Zhou,Yu;Zuo,Jianping;Feng,Huijin;Li,Yuanchao[BioorganicandMedicinalChemistry,2008,vol.16,#5,p.2403-2411]

[5]Mehta,G.etal.[Tetrahedron,1973,vol.29,p.1119-1125]

[6]Banerji,Asoke;Chintalwar,GajananJ.[Phytochemistry,1983,vol.22,#9,p.1945-1948]

[7]Bhan;Soman;Dev[AgriculturalandBiologicalChemistry,1980,vol.44,#7,p.1483-1487]

[8]Takano;Shimazaki;Ogasawara[TetrahedronLetters,1990,vol.31,#23,p.3325-3326]

[1]Esumi,Tomoyuki;Yamamoto,Chihiro;Fukuyama,Yoshiyasu[Synlett,2013,vol.24,#14,p.1845-1847]

[2]Takao,Ken-Ichi;Shu,Sakamoto;Touati,MarianneAyaka;Kusakawa,Yusuke;Tadano,Kin-Ichi[Molecules,2012,vol.17,#11,p.13330-13344]

[3]Xu,Qian-Qian;Zhao,Qun;Shan,Guang-Sheng;Yang,Xi-Cheng;Shi,Qi-Yuan;Lei,Xinsheng[Tetrahedron,2013,vol.69,#50,p.10739-10746]

[4]Takano;Shimazaki;Ogasawara[TetrahedronLetters,1990,vol.31,#23,p.3325-3326]

[5]Locationinpatent:schemeortableEsumi,Tomoyuki;Shimizu,Hiroyuki;Kashiyama,Akinori;Sasaki,Chizu;Toyota,Masao;Fukuyama,Yoshiyasu[TetrahedronLetters,2008,vol.49,#48,p.6846-6849]

[6]Xiong,Yang;Zhang,Guozhu[OrganicLetters,2016,vol.18,#19,p.5094-5097]

[1]Bhan;Soman;Dev[AgriculturalandBiologicalChemistry,1980,vol.44,#7,p.1483-1487]

Literature

Title: Bakuchiol sensitizes cancer cells to TRAIL through ROS- and JNK-mediated upregulation of death receptors and downregulation of survival proteins.

Journal: Biochemical and biophysical research communications 20160429

Title: Bakuchiol augments MyoD activation leading to enhanced myoblast differentiation.

Journal: Chemico-biological interactions 20160325

Title: Characterization of glutathione conjugates derived from reactive metabolites of bakuchiol.

Journal: Chemico-biological interactions 20160125

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: [Metabolic detoxification of bakuchiol is mediated by cytochrome P450 enzymes in human liver microsomes].

Journal: Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences 20120618

Title: Phenolic compounds isolated from Psoralea corylifolia inhibit IL-6-induced STAT3 activation.

Journal: Planta medica 20120601

Title: Bakuchiol derivatives as novel and potent cytotoxic agents: a report.

Journal: European journal of medicinal chemistry 20120301

Title: Estrogenic activities of Psoralea corylifolia L. seed extracts and main constituents.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20110315

Title: Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line.

Journal: European journal of pharmacology 20100925

Title: Isolation and anti-inflammatory activity of Bakuchiol from Ulmus davidiana var. japonica.

Journal: Journal of medicinal food 20100801

Title: Novel bisstyryl derivatives of bakuchiol: targeting oral cavity pathogens.

Journal: European journal of medicinal chemistry 20100701

Title: In vivo pharmacokinetics of bakuchiol after oral administration of bakuchiol extraction in rat plasma.

Journal: Journal of ethnopharmacology 20100421

Title: [Vitro antitumor activity and synthesis of the key intermediate of bakuchiol].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20100401

Title: Targeting tumor proteasome with traditional Chinese medicine.

Journal: Current drug discovery technologies 20100301

Title: Inhibitory effects of bakuchiol, bavachin, and isobavachalcone isolated from Piper longum on melanin production in B16 mouse melanoma cells.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Two antifungal components isolated from Fructus Psoraleae and Folium Eucalypti Globuli by bioassay-guided purification.

Journal: The American journal of Chinese medicine 20100101

Title: Ethanol extract of Psoralea corylifolia L. and its main constituent, bakuchiol, reduce bone loss in ovariectomised Sprague-Dawley rats.

Journal: The British journal of nutrition 20090401

Title: Bakuchiol, an antibacterial component of Psoralidium tenuiflorum.

Journal: Natural product research 20090101

Title: Bakuchiol analogs inhibit monoamine transporters and regulate monoaminergic functions.

Journal: Biochemical pharmacology 20080501

Title: Chemical fingerprint and quantitative analysis of fructus psoraleae by high-performance liquid chromatography.

Journal: Journal of separation science 20070401

Title: Bakuchiol-induced caspase-3-dependent apoptosis occurs through c-Jun NH2-terminal kinase-mediated mitochondrial translocation of Bax in rat liver myofibroblasts.

Journal: European journal of pharmacology 20070322

Title: [Studies on chemical constituents in rhizome of Elaeagnus bockii I].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060601

Title: Protective effect of (S)-bakuchiol from Psoralea corylifolia on rat liver injury in vitro and in vivo.

Journal: Planta medica 20050601

Title: Antioxidant activity of bakuchiol: experimental evidences and theoretical treatments on the possible involvement of the terpenoid chain.

Journal: Chemical research in toxicology 20030901

Title: [Constituent of natural food additive hokosshi extract and an analytical method for the additive in foods].

Journal: Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20021201

Title: Antioxidative components of Psoralea corylifolia (Leguminosae).

Journal: Phytotherapy research : PTR 20020901

Title: The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis.

Journal: Journal of ethnopharmacology 20020101

Title: Bakuchiol: a hepatoprotective compound of Psoralea corylifolia on tacrine-induced cytotoxicity in Hep G2 cells.

Journal: Planta medica 20011101

Title: 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.

Title: 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.

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

Title: 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.

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