14031-37-9

Basic information

• Product Name: Squalene-2,3-diol
• Synonyms: Squalene-2,3-diol;Squalene-2,3-glycol
• CAS NO: 14031-37-9
• Molecular Formula: C₃₀H₅₂O₂
• Molecular Weight: 444.73268
• Mol File: 14031-37-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 550.9±38.0 °C(Predicted)
• Appearance: /
• Density: 0.914±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• PKA: 14.66±0.29(Predicted)
• CAS DataBase Reference: Squalene-2,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: Squalene-2,3-diol(14031-37-9)
• EPA Substance Registry System: Squalene-2,3-diol(14031-37-9)

Safety Data

• Hazardous Substances Data: 14031-37-9(Hazardous Substances Data)

Usage

Uses

Squalene-2,3-glycol is an intermediate in the enzymic conversion of squalene to lanosterol and cholesterol, and a precursor in the chemical synthesis of different squalene oxides.

Upstream product

• 14050-42-1 2,3-Oxidosqualene 
• 111-02-4 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene 
• 65746-05-6 squalene monobromohydrin: 3-bromo-2,6,10,15,19,23-hexamethyl-6,10,14,18,22-tetracosapentaen-2-ol (all E) 

Downstream Products

• 63955-78-2 (E, S)-3,7-dimethyl- oct-2-ene-1,6,7-triol 
• 63955-79-3 (E, R)-3,7-dimethyl- oct-2-ene-1,6,7-triol 
• 819073-79-5 (3S)-2,3-dihydroxy-2,3-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate 
• 819073-80-8 (3R)-2,3-dihydroxy-2,3-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate 

Relevant articles and documents

Enzymatic cyclizations of squalene analogs with threo- And erythro-diols at the 6,7- or 10,11-positions by recombinant squalene cyclase. Trapping of carbocation intermediates and mechanistic insights into the product and substrate specificities

In order to trap the carbocation intermediates formed during the squalene cyclization cascade, squalene analogs with threo- and erythro-dioh at the 6,7- and 10,11-positions were incubated with the recombinant squalene cyclase from Alicyclobacillus acidocaldarius, leading to the construction of the triterpenes with tetrahydropyran, octahydrochromene, decahydronaphthalene with a carbonyl group, dodecahydrobenzo[f]chromene, tetradecahydronaphtho[2,1-b]oxepine and malabaricane skeletons, almost of which are novel compounds. These products indicate that 6-membered monocyclic, 6/6-fused bicyclic and 6/6/5-fused tricyclic cations were involved in the cyclization reaction in addition to acyclic cation. All the trapped cations were the stable tertiary cation, but not the secondary one, indicating that the polycyclization reaction proceeds with a Markovnikov closure. The product profiles revealed that the cyclization reactions proceeded with the product and substrate specificities in addition to enantioselectivity. Mechanistic insight into the observed stereochemical specificities indicated that the pre-organized chair-conformation of squalene-diols is tightly constricted by the cyclase and a free motion or a conformational change is not allowed in the reaction cavity, thus, the substrate and product specificities are dominantly directed by the least motion of the nucleophilic hydroxyl group toward the intermediary carbocation; a small rotation of the hydroxyl group afforded the cyclization products in a good yield, but a large rotation of the hydroxyl group gave a marginal or no detectable amount of products. The Royal Society of Chemistry 2005.

Biosynthesis of β-Amyrin. Part 2. The in vitro Cyclization of 22,23-dihydro-methylenesqualene 2,3-epoxide to 30-nor-29,29-dimethyl-18β-olean-12-en-3β-ol by Microsomes from Pisum sativum

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