67314-15-2

Basic information

• Product Name: petrosterol
• Synonyms: petrosterol;(24R)-24-[(1R,2R)-2-Methylcyclopropyl]-26,27-dinorcholest-5-en-3β-ol
• CAS NO: 67314-15-2
• Molecular Formula: C₂₉H₄₈O
• Molecular Weight: 412.6908
• Mol File: 67314-15-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 506°Cat760mmHg
• Flash Point: 219.7°C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 2.34E-12mmHg at 25°C
• Refractive Index: 1.538
• CAS DataBase Reference: petrosterol(CAS DataBase Reference)
• NIST Chemistry Reference: petrosterol(67314-15-2)
• EPA Substance Registry System: petrosterol(67314-15-2)

Safety Data

• Hazardous Substances Data: 67314-15-2(Hazardous Substances Data)

Usage

General Description

Petrosterol is a chemical compound derived from the refining of crude oil and is commonly used in the production of lubricants and synthetic oils. It is a complex mixture of hydrocarbons and compounds, including wax esters, fatty acids, and alcohols. Petrosterol has a high viscosity, making it ideal for applications where a thick and durable lubricant is required, such as in industrial machinery and automotive engines. Its chemical composition also allows it to provide excellent resistance to temperature extremes and oxidation, making it suitable for use in high-performance and long-lasting lubricants. Additionally, petrosterol has low toxicity and is considered safe for use in various industrial and consumer products.

InChI:InChI=1/C29H48O/c1-18(24-16-20(24)3)6-7-19(2)25-10-11-26-23-9-8-21-17-22(30)12-14-28(21,4)27(23)13-15-29(25,26)5/h8,18-20,22-27,30H,6-7,9-17H2,1-5H3/t18-,19-,20-,22+,23+,24+,25-,26+,27+,28+,29-/m1/s1

Upstream product

• 99477-98-2 (4R,5R,8R)-4-Methanesulfonyloxy-8-((3bS,6R,8aS,8bS,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-5-methyl-nonanoic acid isopropyl ester 
• 99477-96-0 (E)-(4S,5R,8R)-4-Hydroxy-8-((3bS,6R,8aS,8bS,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-5-methyl-non-6-en-2-ynoic acid isopropyl ester 
• 99478-01-0 Methanesulfonic acid (1R,2S)-2-[(1R,4R)-4-((3bS,6R,8aS,8bS,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-1-methyl-pentyl]-cyclopropylmethyl ester 
• 99477-97-1 (4R,5R,8R)-4-Hydroxy-8-((3bS,6R,8aS,8bS,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-5-methyl-nonanoic acid isopropyl ester 
• 99478-00-9 {(1R,2S)-2-[(1R,4R)-4-((3bS,6R,8aS,8bS,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-1-methyl-pentyl]-cyclopropyl}-methanol 
• 99478-02-1 (3bS,6R,8aS,8bS,10aR)-10-Methoxy-3a,5a-dimethyl-6-[(1R,4R)-1-methyl-4-((1R,2R)-2-methyl-cyclopropyl)-pentyl]-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene 
• 91228-99-8 (24R,25R,26R)-24-hydroxymethyl-26-methyl-6β-methoxy-3α,5:25,27-dicyclo-5α-cholestane 
• 91228-92-1 triphenylphopshoranilidenemethyl (2'-methyl)cyclopropyl ketone 
• 42274-66-8 trans-2-methylcyclopropanecarboxylic acid chloride 
• 182949-25-3 (2S,5R)-2-[(3S,8S,9S,10R,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-((1R,2R)-2-methyl-cyclopropyl)-hexan-2-ol 
• 182949-19-5 Methanesulfonic acid (1R,2R)-4-benzyloxy-1-(2-cyano-ethyl)-2-methyl-butyl ester 
• 182949-14-0 [(R)-1-((R)-3-Benzyloxy-1-methyl-propyl)-4-methyl-pent-3-enyloxy]-tert-butyl-dimethyl-silane 
• 182949-15-1 (3R,4R)-6-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexanal 
• 1027248-91-4 Methanesulfonic acid (1R,2S)-2-((R)-3-benzyloxy-1-methyl-propyl)-cyclopropylmethyl ester 

Downstream Products

• 1186642-40-9 5α,6α-epoxy-petrosterol 
• 91279-37-7 (24R,25R)-24-methyl-26-methylenecholest-5-en-3β-ol 
• 91229-05-9 (E)-24-methyl-26,26-dimethyl-27-norcholesta-5,23-dien-3β-ol 
• 91229-04-8 (Z)-24-methyl-26,26-dimethyl-27-norcholesta-5,23-dien-3β-ol 
• 91229-07-1 (24S)-24-methyl-26,26-dimethyl-27-norcholesta-5,22-dien-3β-ol 
• 91229-06-0 (24S,25R)-24,26-dimethylcholesta-5,22-dien-3β-ol 
• 124512-49-8 (24R,25R,26R)-3β-methoxy-24,26-dimethyl-25,27-cyclo-5α-cholestane 
• 83187-97-7 (24R,25R,26R)-petrosterol acetate 
• 91279-33-3 (24R,25R)-5,6-dihydro-5α-aplysterol 
• 106518-69-8 5α-petrostan-3β-ol 

Relevant articles and documents

Stereoselective synthesis of petrosterol and a formal synthesis of aragusterols

Stereoselective construction of a steroidal side chain containing a 26-27 cyclopropane ring, compound 22, has been achieved by an intramolecular cyclisation of the corresponding β-methylsulfonyloxy cyanide 16, derived from a chiral cyclopentane derivative. Compound 22 has been further utilised in the synthesis of the naturally occurring steroid petrosterol 3.

Stereochmical Effects in Cyclopropane Ring Openings: Synthesis and Isomerization of Petrosterol and All Three of Its Trans Cyclopropane Diastereomers

All four trans isomers of the marine sterol petrosterol, with a side chain terminating in a cyclopropane ring, have been synthesized.The absolute stereochemistry of the diastereomers was determined by correlation with compounds of known absolute stereochemistry.The product distribution resulting from the acid-catalyzed isomerization of these four diastereomers shows a marked dependence on the relative stereochemistry between the cyclopropane ring and the adjacent chiral center at C24.A careful examination of the conformations available to the side chain leads to a rational explanation of this dependence, and sheds light on hitherto unrecognized subtle stereochemical features operating among aliphatic cyclopropanes.In addition we report the synthesis and acid-catalyzed ring opening of (24S,25S,26S)-22,22-dideuteriopetrosterol and the confirmation by this labeling study that one of the products of the isomerization reaction arises via a 1,5-hydride-shift mechanism.