10309-37-2

Usage

InChI: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

Upstream product

• 110-93-0 6-Methyl-hept-5-en-2-on 
• 104846-78-8 3,7-dimethyl-oct-6-en-1-yn-3-yl methyl carbonate 
• 106-24-1 Geraniol 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 105460-59-1 methyl 2-{4-[(tert-butyldimethylsilyl)oxy]phenyl}acetate 
• 17015-63-3 (S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 6138-90-5 trans-geranyl bromide 
• 80-59-1 Tiglic acid 
• 485385-65-7 (S)-2-ethenyl-2,6-dimethylhept-5-en-1-ol 
• 1492057-03-0 C₂₇H₃₈OSi 
• 1492057-02-9 (S)-((2-(2-bromoethyl)-2-methylbut-3-en-1-yl)oxy)(tert-butyl)diphenylsilane 
• 1492057-01-8 (S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methylpent-4-en-1-ol 
• 1492056-99-1 (S)-tert-butyl 3-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methylpent-4-enoate 

Downstream Products

• 43010-52-2 7,8,16,17-tetrahydrobakuchiol 
• 43010-50-0 7,8-dihydrobakuchiol 
• 10309-38-3 4-(3-ethyl-3,7-dimethyloctyl)phenol 
• 74921-91-8 bakuchiol ethyl ether 
• 74921-92-9 (S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-propoxybenzene 
• 1026776-51-1 C₁₉H₂₄O₂ 
• 1026776-58-8 (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-2-nitrophenol 
• 1026776-43-1 12,13-diolbakuchiol 
• 1028939-07-2 C₄₁H₆₀O₃ 
• 1234320-93-4 4-{3-(4-hydroxystyryl)-3,7-dimethylocta-1,6-dienyl}phenol 
• 1234320-92-3 (R)-4-{3-(4-methoxystyryl)-3,7-dimethylocta-1,6-dienyl}phenol 
• 1361320-38-8 (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenyl propionate 
• 1361320-43-5 (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenyl decanoate 

Relevant academic research and scientific papers

Synthesis of (±)-Bakuchiol via a pot-economy approach

A rapid synthetic route toward (±)-Bakuchiol is presented in 29% overall yield. After the sole all-carbon quaternary carbon center is created via allylboration of 2-aryl acetaldehyde, a “Pot-Economy” approach including mesylation, elimination, and desilylation was realized in the presence oftBuOK under ambient temperature to provide (±)-Bakuchiol.

Enantioselective Synthesis of Quaternary Stereocenters via Chromium Catalysis

Asymmetric allylation of aldehydes with γ-disubstituted allyl halides has been achieved in the presence of a sulfonamide/oxazoline chromium complex. A variety of synthetically useful α-homoallylic alcohols with two consecutive stereogenic centers, including one quaternary carbon, can be accessed in a highly diastereoselective and enantioselective manner.

A short synthesis of (+)-bakuchiol

The concise enantioselective total synthesis of (+)-bakuchiol has been achieved using an asymmetric 1,4-addition to construct its all-carbon chiral quaternary center based on the induction of chirality by the (2′S)-2′-phenyloxazolidinone auxiliary, followed by a one-pot transformation under aldol reaction conditions. The synthesis was completed in four steps from (E)-geranic acid in an overall yield of 53%. Georg Thieme Verlag Stuttgart · New York.

A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol

A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol, and ent-Bakuchiol is described through one common intermediate bearing a chiral all-carbon quaternary carbon center, which involves stereoselectively unconjugated alkylation of the α,β-unsaturated imide bearing Evans' auxiliary, Takai-Utimoto reaction, Negishi reaction, and Heck reaction as key steps.

Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol

An asymmetric Claisen rearrangement using Oppolzer's camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.

Stereoselective total synthesis of natural (S)-bakuchiol and its enantiomer

A practical stereoselective synthesis of (S)-bakuchiol (1) and its enantiomer is reported. The important intermediate, (R)-configured β-siloxy aldehyde 5, was obtained in three steps from the easily available material geraniol (2) via the key step of Yamamoto's rearrangement of epoxy silyl ethers. (S)-Bakuchiol (1) and its enantiomer, (R)-bakuchiol (17), were finally obtained in different synthetic sequences with overall yields of 51% (ten steps) and 40% (nine steps) from geraniol (2), respectively.

Efficient construction of a chiral all-carbon quaternary center by asymmetric 1,4-addition and its application to total synthesis of (+)-bakuchiol

The conjugate addition of lithium divinylcuprate to (4S,2′E)-3-(6′-TBDPS-3′-methylhex-2′-enoyl)-4-phenyloxazolidin-2-one proceeded efficiently to create a chiral all-carbon quaternary center with a high diastereoselectivity (R:S = 95:5). The absolute configuration of the newly generated chiral center was confirmed by applying this methodology to the total synthesis of (+)-bakuchiol.

Synthesis and structure-immunosuppressive activity relationships of bakuchiol and its derivatives

A series of derivatives of bakuchiol were synthesized and tested in vitro for their cytotoxicity, and inhibition of T cell proliferation and B cell proliferation. The data obtained provided preliminary structure-activity relationships of the compounds as immunosuppressive activity.

Pharmaceutical compounds for treating copd

Use of an MPO inhibitor for the treatment of COPD.

Enantiocontrolled synthesis of natural (+)-bakuchiol

(+)-Bakuchiol (1), an irregular phenolic monoterpene of Psoralea corylifolia L., has been first synthesized in natural forms starting from (S)-O-benzylglycidol (2).