80-99-9

Basic information

• Product Name: LATHOSTEROL
• Synonyms: (3-beta,5-alpha)-cholest-7-en-3-o;3beta-Hydroxy-5alpha-cholest-7-ene;7-Cholesten-3-beta-ol;Cholest-7-en-3-ol;Cholest-7-en-3-ol, (3beta,5alpha)-;delta(Sup7)-Cholestenol;DELTA7-Cholestenol;gamma-cholesterol
• CAS NO: 80-99-9
• Molecular Formula: C₂₇H₄₆O
• Molecular Weight: 386.65
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 80-99-9.mol

Chemical Properties

• Melting Point: 126°C
• Boiling Point: 452.8°C (rough estimate)
• Flash Point: 208.9 ºC
• Appearance: /
• Density: 0.9610 (rough estimate)
• Vapor Pressure: 3.32E-11mmHg at 25°C
• Refractive Index: 1.5250 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: LATHOSTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: LATHOSTEROL(80-99-9)
• EPA Substance Registry System: LATHOSTEROL(80-99-9)

Safety Data

• WGK Germany: 3
• RTECS: FZ7000000
• Hazardous Substances Data: 80-99-9(Hazardous Substances Data)

Usage

Uses

Used in Health Assessment:
Lathosterol is used as a biomarker for cholesterol synthesis and absorption, indicating deteriorating health when its levels decrease along with sitosterol and cholesterol. Low levels of lathosterol, sitosterol, and cholesterol predict mortality additively and independently of each other.
Used in Cholesterol and Plant Sterols Estimation:
Lathosterol has been used as a standard for estimating the concentrations of cholesterol and plant sterols, helping in the assessment of cholesterol metabolism and related health conditions.
Used in Enzymatic Assays:
5α-Cholest-7-en-3β-ol, the chemical name for lathosterol, is used as a substrate in enzymatic assays for plasma cholesterol, aiding in the study and measurement of cholesterol levels in the blood.
Used in Ecological Studies:
Lathosterol has been used to supplement the diet of Daphnia galeata, a small freshwater crustacean, to study its effects on life-history traits. This application helps in understanding the ecological impact of cholesterol and its precursors on aquatic organisms.

Biochem/physiol Actions

5α-Cholest-7-en-3β-ol (Lathosterol) is an intermediate in cholesterol biosynthesis pathway. Lathosterol in serum is carried on lipoproteins and is indicative of the rate of cholesterol synthesis. It acts as a marker of synthesis of cholesterol and is not affected by dietary consumption of cholesterol.

InChI:InChI=1/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 434-16-2 7-dehydrocholesterol 
• 15459-85-5 5α-cholest-7-en-3-one 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 64-17-5 ethanol 
• 6038-38-6 3β,7β-bis-benzoyloxy-cholest-5-ene 
• 809-51-8 7-ketocholesteryl acetate 
• 57-88-5 cholesterol 
• 16826-37-2 5α-cholest-7-ene-3β-ol acetate 
• 137637-33-3 5α-cholesta-6,8-dien-3β-ol 
• 566-27-8 cholest-5-en-3β,7β-diol 
• 40823-41-4 acetic acid-(7α-hydroxy-5α-cholestanyl-(3β)-ester) 

Downstream Products

• 15459-85-5 5α-cholest-7-en-3-one 
• 566-96-1 cholesta-7,9(11)-dien-3β-ol 
• 20780-35-2 5α-cholest-14-en-3β-ol 
• 6562-21-6 3β-(Acetyloxy)-5α-cholest-8(14)-ene 
• 16826-37-2 5α-cholest-7-ene-3β-ol acetate 
• 73389-49-8 5α,14α-cholestane-3β,15α-diol 
• 40071-65-6 5α-cholest-7-ene 
• 6673-64-9 5α-cholesta-2,7-diene 
• 16826-35-0 cholesta-4,7-dien-3-one 
• 6618-17-3 3β-(toluene-4-sulfonyloxy)-5α-cholest-7-ene 
• 4356-22-3 5α-cholest-7-en-3β-yl benzoate 

Relevant articles and documents

Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis in Locusta migratoria

We have synthesized a tritiated form of 14α-hydroxy-5β-cholest-7-ene-3,6-dione (5β-diketol) of high specific activity (1.74 TBq/mmol) from 7-dehydrocholesterol in seven steps with stereoselective introduction of the A/B cis ring junction as the key reaction. We have examined the ability of endocrine glands (prothoracic glands) of Locusta migratoria to use this molecule as a precursor of 3-dehydroecdysone and of ecdysone biosynthesis. A very efficient conversion of 5β-diketol to ecdysone and to 3-dehydroecdysone was monitored, which opens up new possibilities for the understanding of the role of 3-dehydro-compounds in ecdysteroid biosynthesis.

Epoxide Cleavage Reactions of 7α,8α- and 7β,8β-Epoxycholestanol Acetates

In a search for an alternative synthetic route to 32-oxygenated sterol derivatives such as 5, 7α,8α- and 7β,8β-epoxycholestanol acetate (9 and 10) were subjected to various conditions of epoxide cleavage.The trans-diaxial opening of the α-epoxide 9 with lithium/ethylamine gave the 7α-ol 11, whereas the 8β-ol 12 was produced from the β-epoxide 10 on reduction with lithium aluminum hydride.However, the trans-diaxal 8β-halo(or hydroxy)-7α-ols were not obtained at all on treatment of the α-epoxide 9 with various mineral acids or BF3-etherate in benzene.Under these conditions, the C-8 carbenium ion would be the intermediate, from which the 7-ketone 13 and a mixture of Δ6,8-, Δ7,14- and/or Δ8,14-diene compounds 16, as well as Δ8(9)- and Δ8(14)-7α-ol 14 and 4a, were produced.The latter allylic alcohol 4a, a possible synthetic precursor of 32-oxygenated sterol was prepared in 63percent yield when benzene was replaced with tetrahydrofuran in the BF3-etherate-catalyzed reaction of the α-epoxide 9.Keywords-epoxide cleavage; 32-oxygenated sterol; 7α,8α-epoxycholestanol acetate; 7β,8β-epoxycholestanol acetate; 3β-acetoxycholest-8(14)-en-7α-ol; reduction; acid treatment; boron trifluoride-etherate; long-range 13C-1H COSY