71761-06-3

Usage

Uses

Used in Pharmaceutical Industry:
(5Z,7E)-9,10-Secostigmasta-5,7,10(19)-trien-3β-ol is used as a precursor compound for the synthetic preparation of 1α-Hydroxyvitamin D5, a promising chemopreventive agent for breast cancer. Its unique structure allows for the development of novel therapeutic agents with potential applications in cancer prevention and treatment.
Used in Nutritional Supplements:
As a plant sterol, (5Z,7E)-9,10-Secostigmasta-5,7,10(19)-trien-3β-ol may be used as an ingredient in nutritional supplements, particularly those aimed at promoting cardiovascular health and maintaining healthy cholesterol levels. Its presence in the diet can help to lower the absorption of dietary cholesterol, thus contributing to overall health and well-being.
Used in Cosmetics Industry:
Due to its potential anti-inflammatory and skin-soothing properties, (5Z,7E)-9,10-Secostigmasta-5,7,10(19)-trien-3β-ol may also find applications in the cosmetics industry. It could be used as an active ingredient in skincare products, targeting skin health and providing anti-aging benefits.

InChI:InChI=1/C29H48O/c1-7-23(20(2)3)12-10-22(5)27-16-17-28-24(9-8-18-29(27,28)6)13-14-25-19-26(30)15-11-21(25)4/h13-14,20,22-23,26-28,30H,4,7-12,15-19H2,1-3,5-6H3/b24-13+,25-14-/t22-,23-,26-,27-,28+,29-/m1/s1

Upstream product

• 521-04-0 stigmastadien-(5.7)-ol-(3β) 
• 71-43-2 benzene 
• 59157-68-5 3β,7β-dibenzoyloxy-stigmastene-(5) 
• 865539-85-1 Acetic acid (S)-3-[2-[(1R,3aS,7aR)-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 
• 915-05-9 stigmast-5-en-3-yl acetate 
• 54200-16-7 Acetic acid (3S,8S,9S,10R,13R,14S,17R)-7-bromo-17-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 521-04-0 Δ⁵-stigmasterol 
• 4863-54-1 5-stigmasten-3β,7β-diol 
• 6020-61-7 3β-O-acetyl-5,7-dienesitosterol 

Downstream Products

• 865539-87-3 9,10-seco-stigmasta-5(E),7(E),10(19)-trien-3β-ol 
• 865539-88-4 3β-triethylsilyloxy-9,10-seco-stigmasta-5(E),7(E),10(19)-triene 

Relevant academic research and scientific papers

1α-Hydroxyvitamin D5, its synthesis and use in cancer prevention

A compound of formula I: wherein R1 is hydrogen, R2 is —CH3, R3 is —CH3, and R4 is hydrogen, useful in cancer prevention and therapy.

Synthesis of 1α-Hydroxyvitamin D5 using a modified two wavelength photolysis for vitamin D formation

1α-Hydroxyvitamin D5 (1) is a promising chemopreventive agent for breast cancer and is being developed as a drug. We report a synthesis for this vitamin D analogue which uses a photochemical method for the B-ring opening, leading to the conjugated triene system. The precursor 7-dehydrositosteryl acetate (4) obtained through a one-pot, five-step procedure, was completely free of the 4,6-diene isomer that usually forms in the 5,7-diene synthesis. The pre-vitamin isomer (11) was generated using a modified two-wavelength photolysis procedure that increases the yield for this step more than 3-fold compared to classically used photolysis. The 1α-hydroxylation step was performed on the 3-triethylsilyl-trans-vitamin D5 (17) obtained via the sulfur dioxide adduct of cis-vitamin D5, in an overall yield of 48%. Photoisomerization and deprotection completed the synthesis.