67314-15-2

Usage

Uses

Used in Lubricant Production:
Petrosterol is used as a base material for the production of lubricants and synthetic oils due to its high viscosity and excellent resistance to temperature extremes and oxidation. This makes it suitable for use in various industrial machinery and automotive engines where a durable and long-lasting lubricant is required.
Used in Industrial Machinery:
Petrosterol is used as a lubricant in industrial machinery for its ability to provide a thick and durable layer of protection against friction and wear, ensuring the smooth operation and longevity of the machinery.
Used in Automotive Engines:
Petrosterol is used as a lubricant in automotive engines to protect the engine components from friction and wear, as well as to provide resistance to temperature extremes and oxidation, ensuring the engine's performance and longevity.
Used in High-Performance Lubricants:
Petrosterol is used as a key ingredient in high-performance lubricants due to its excellent resistance to temperature extremes and oxidation, making it suitable for use in demanding applications where conventional lubricants may not be sufficient.
Used in Consumer Products:
Petrosterol is used in various consumer products due to its low toxicity and safety profile, making it an ideal choice for use in products that come into contact with the skin or are used in sensitive environments.

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

• 91229-00-4 Toluene-4-sulfonic acid (2R,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1R,2R)-2-methyl-cyclopropyl)-hexyl ester 
• 144781-81-7 methyl (3S,4R)-4-(tert-butyldimethylsiloxy)-3,7-dimethyl-6-octenoate 
• 144781-72-6 (1R,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(1-chloro-1-methyl-ethyl)-2-methyl-cyclopentanecarboxylic acid methyl ester 
• 171595-15-6 (1R,2R)-2-<(1R)-3-Hydroxy-1-methylpropyl>-1-methylcyclopropane 
• 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 

Downstream Products

• 106518-69-8 5α-petrostan-3β-ol 
• 91279-33-3 (24R,25R)-5,6-dihydro-5α-aplysterol 
• 124512-49-8 (24R,25R,26R)-3β-methoxy-24,26-dimethyl-25,27-cyclo-5α-cholestane 
• 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 
• 83187-97-7 (24R,25R,26R)-petrosterol acetate 

Relevant academic research and scientific papers

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.

Stereocontrolled Synthesis of Petrosterol

Petrosterol (1), a cyclopropane-containing C29 marine sterol, has been synthesiyed in a stereocontrolled manner which involves -Wittig rearrangement of the propargyl ether (3) yielding the acetylene alcohol (4) with the required C-24, 25 stereochemistry.

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.