87720-90-9

Basic information

• Product Name: (R)-(+)-1,2-OCTANEDIOL
• Synonyms: (R)-(+)-1,2-OCTANEDIOL;(2R)-1,2-Octanediol;(R)-Octane-1,2-diol
• CAS NO: 87720-90-9
• Molecular Formula: C₈H₁₈O₂
• Molecular Weight: 146.23
• Product Categories: Chiral Building Blocks;Organic Building Blocks;Polyols
• Mol File: 87720-90-9.mol
• Article Data: 54

Chemical Properties

• Boiling Point: 243 °C at 760 mmHg
• Flash Point: 113 °C
• Appearance: /
• Density: 0.937 g/cm³
• CAS DataBase Reference: (R)-(+)-1,2-OCTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1,2-OCTANEDIOL(87720-90-9)
• EPA Substance Registry System: (R)-(+)-1,2-OCTANEDIOL(87720-90-9)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 87720-90-9(Hazardous Substances Data)

Usage

General Description

(R)-(+)-1,2-OCTANEDIOL is a chemical compound with the molecular formula C8H18O2. It is a colorless, viscous liquid that is commonly used as a solvent, humectant, and coupling agent in various industrial and consumer products. (R)-(+)-1,2-OCTANEDIOL is optically active, meaning it has a specific rotation of plane-polarized light. It is often used in the production of resins, plasticizers, and lubricants, as well as in the synthesis of pharmaceuticals and agrochemicals. (R)-(+)-1,2-OCTANEDIOL has also been studied for its antimicrobial and antifungal properties, making it a potential ingredient in personal care and cosmetic products. Furthermore, it is considered to be relatively safe for use and has low toxicity, making it a versatile and valuable chemical in many different applications.

Upstream product

• 1117-86-8 1,2-octandiol 
• 111-66-0 oct-1-ene 
• 105581-81-5 (S)-2-Methoxy-octan-1-ol 
• 137958-57-7 (S)-2-Benzyloxy-octan-1-ol 
• 92572-72-0 2-(1S-hydroxyheptyl)-1,3-oxathiane 
• 141339-65-3 Benzoic acid (S)-2-hydroxy-octyl ester 
• 18409-17-1 (E)-oct-2-en-1-ol 
• 192766-68-0 (E)-(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-hydroxy-hept-4-en-1-one 
• 205264-70-6 (S)-2-acetoxyoctanoic acid ethyl ester 
• 2984-50-1 1,2-Epoxyoctane 
• 124-63-0 methanesulfonyl chloride 
• 65-85-0 benzoic acid 
• 111423-32-6 (E)-1-hexyl-3-hydroxy-4,4,4-trifluoro-1-butene 
• 110994-93-9 (S)-(-)-hydroxy-2 octanoate d'ethyle 

Downstream Products

• 1215184-66-9 4-R-4-n-hexyl-2-phenyl-1,3-dioxolane 
• 111221-79-5 (S)-(-)-2-hydroxyoctyl tosylate 
• 111221-79-5 (R)-(+)-2-hydroxyoctyl tosylate 
• 77495-66-0 (R)-1,2-epoxyoctane 
• 5978-70-1 (R)-Octan-2-ol 
• 6169-06-8 (S)-2-Octanol 
• 1198777-92-2 (R)-octane-1,2-diyl dibenzoate 
• 158761-00-3 mniopetal C 
• 1450835-70-7 C₂₄H₃₆O₂Si 

Relevant articles and documents

Structure-Guided Regulation in the Enantioselectivity of an Epoxide Hydrolase to Produce Enantiomeric Monosubstituted Epoxides and Vicinal Diols via Kinetic Resolution

Structure-guided microtuning of an Aspergillus usamii epoxide hydrolase was executed. One mutant, A214C/A250I, displayed a 12.6-fold enhanced enantiomeric ratio (E = 202) toward rac-styrene oxide, achieving its nearly perfect kinetic resolution at 0.8 M in pure water or 1.6 M in n-hexanol/water. Several other beneficial mutants also displayed significantly improved E values, offering promising biocatalysts to access 19 structurally diverse chiral monosubstituted epoxides (97.1 - ≥ 99% ees) and vicinal diols (56.2-98.0% eep) with high yields.

Raw and waste plant materials as sources of fungi with epoxide hydrolase activity. Application to the kinetic resolution of aryl and alkyl glycidyl ethers

The by-products of olive oil production can be used as sources of microbial strains. Penicillium sp., Aspergillus terreus, Penicillium aurantiogriseum, Aspergillus tubingensis and Aspergillus niger were selected on the basis of their epoxide-hydrolyzing activity towards racemic rac-glycidyl phenyl ether. We studied the effect on enzymatic activity of adding styrene oxide to the growth medium. It induced the biosynthesis of epoxide hydrolases and reduced cell growth. The resolution capacity of the five fungi was tested on rac-glycidyl phenyl ether, rac-benzyl glycidyl ether, rac-1,2-epoxyhexane and rac-1,2-epoxyoctane. The resolution of rac-glycidyl phenyl ether by A. niger, rac-benzyl glycidyl ether by P. aurantiogriseum and A. terreus, rac-1,2-epoxyhexane by A. tubingensis and rac-1,2-epoxyoctane by A. terreus provided (S)-3-phenoxy-1,2-propanediol (45.1% yield, 51.4% ee), (R)-3-benzyloxy-1,2-propanediol (40.8% yield, 43.3% ee), (S)-3-benzyloxy-1,2-propanediol (45.4% yield, 45.6% ee), (R)-1,2-hexanediol (70.4% yield, 24.4% ee) and (R)-1,2-octanediol (21.4% yield, 27.5% ee), respectively. The (R)-enantiopreference of the epoxide hydrolases from P. aurantiogriseum is unprecedented.

Highly Enantioselective Iron-Catalyzed cis-Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-OOH Reactive Intermediate

The development of environmentally benign catalysts for highly enantioselective asymmetric cis-dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L=N,N′-dimethyl-N,N′-bis(2-methyl-8-quinolyl)-cyclohexane-1,2-diamine) as a catalyst, cis-diols in up to 99.8 % ee with 85 % isolated yield have been achieved in AD of alkenes with H2O2as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2]+H2O2” method is applicable to both (E)-alkenes and terminal alkenes (24 examples >80 % ee, up to 1 g scale). Mechanistic studies, including18O-labeling, UV/Vis, EPR, ESI-MS analyses, and DFT calculations lend evidence for the involvement of chiral FeIII-OOH active species in enantioselective formation of the two C?O bonds.