178765-49-6

Basic information

• Product Name: Delta3,2-Hydroxylbakuchiol
• Synonyms: Delta3,2-Hydroxylbakuchiol;13-Hydroxyisobakuchiol;4-[(1E,3S,5E)-3-Ethenyl-7-hydroxy-3,7-dimethyl-1,5-octadienyl]phenol
• CAS NO: 178765-49-6
• Molecular Formula: C18H24O2
• Molecular Weight: 272.38196
• Mol File: 178765-49-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Delta3,2-Hydroxylbakuchiol(CAS DataBase Reference)
• NIST Chemistry Reference: Delta3,2-Hydroxylbakuchiol(178765-49-6)
• EPA Substance Registry System: Delta3,2-Hydroxylbakuchiol(178765-49-6)

Safety Data

• Hazardous Substances Data: 178765-49-6(Hazardous Substances Data)

Usage

Uses

Used in Skincare Industry:
Delta3,2-Hydroxylbakuchiol is used as an anti-aging ingredient for its ability to stimulate collagen and elastin production, improving skin elasticity and reducing the appearance of wrinkles and fine lines. Its anti-inflammatory and antioxidant properties also contribute to promoting overall skin health and combating signs of aging.
Delta3,2-Hydroxylbakuchiol is used as a skin-regenerating agent for its capacity to enhance skin health and rejuvenate the skin's appearance by promoting collagen and elastin synthesis.
Delta3,2-Hydroxylbakuchiol is used as an alternative to retinoids in skincare formulations due to its well-tolerated and safe nature for topical use, offering a promising solution for those seeking to avoid potential side effects associated with retinoids.

Upstream product

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Relevant articles and documents

Δ3 Asymmetric synthesis method -2 - hydroxyl psoralen and analogue compound

The invention belongs to the field of chemical synthesis, provides a novel method for synthesizing delta3-2-hydroxybakuchiol and particularly relates to an asymmetric synthesis method for delta3-2-hydroxybakuchiol and analog compounds. The delta3-2-hydroxybakuchiol and the analog compounds, the general formula of which is (I), are synthesized by an asymmetric synthesis route. Problems in the prior art, that the content of the delta3-2-hydroxybakuchiol obtained by extraction and separation from plants is very low, an extraction rate is very low, the delta3-2-hydroxybakuchiol is prone to oxidative deterioration in extraction and separation processes, and the like, are overcome by the method. The method can provide sufficient samples for related pharmaceutical research, and provides good foundations for pharmaceutical research on antibiosis, infection resistance, oxidation resistance, pigment deposition resistance, reduction of bone loss, immunosuppression, liver damage, sedation and hypnosis, and the like. In the formula (I), R1 is selected from 4-hydroxy, 3-hydroxy, 2-hydroxy, hydrogen, 4-methyl, 4-methoxy, 4-trifluoromethyl, 3,4-[d][1,3]dioxole, and 3,4-phenyl; R2 is selected from methyl, ethyl, and butyl; and R3 is selected from vinyl, ethyl and cyclopropyl.

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.

Synthesis of racemic Δ3-2-hydroxybakuchiol and its analogues

The first synthetic approach to (±)-Δ3-2- hydroxybakuchiol (=4-[(1E,5E)-3-ethenyl-7-hydroxy-3,7-dimethylocta-1,5-dien-1- yl]phenol; 14) and its analogues 13a - 13f was developed by 12 steps (Schemes 2 and 3). The key features of the approach are the construction of the quaternary C-center bearing the ethenyl group by a Johnson - Claisen rearrangement (→6); and of an (E)-alkenyl iodide via a Takai - Utimoto reaction (→11); and an arylation via a Negishi cross-coupling reaction (→12e - 12f).