78672-90-9

Basic information

• Product Name: (R)-Methyl 3-Hydroxyoctanoate
• Synonyms: (R)-Methyl 3-Hydroxyoctanoate;FHWBTAQRRDZDIY-MRVPVSSYSA-N
• CAS NO: 78672-90-9
• Molecular Formula: C₉H₁₈O₃
• Molecular Weight: 174.23742
• Mol File: 78672-90-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 259.9±13.0 °C(Predicted)
• Appearance: /
• Density: 0.976±0.06 g/cm3(Predicted)
• PKA: 14.09±0.20(Predicted)
• CAS DataBase Reference: (R)-Methyl 3-Hydroxyoctanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Methyl 3-Hydroxyoctanoate(78672-90-9)
• EPA Substance Registry System: (R)-Methyl 3-Hydroxyoctanoate(78672-90-9)

Safety Data

• Hazardous Substances Data: 78672-90-9(Hazardous Substances Data)

Usage

Description

(R)-Methyl 3-Hydroxyoctanoate, with the molecular formula C9H18O3, is a colorless liquid characterized by a sweet, fruity odor. It is an ester compound that is widely recognized for its distinct aroma and taste, making it a popular choice in the flavor and fragrance industry.

Uses

Used in Flavor and Fragrance Industry:
(R)-Methyl 3-Hydroxyoctanoate is used as a flavor and fragrance ingredient for its characteristic sweet, fruity scent and taste. It enhances the sensory experience of various products, contributing to their overall appeal.
Used in Food and Beverage Industry:
(R)-Methyl 3-Hydroxyoctanoate is used as an additive in the food and beverage industry to impart a pleasant aroma and taste to products, making them more enjoyable for consumers.
Used in Cosmetic and Personal Care Industry:
(R)-Methyl 3-Hydroxyoctanoate is used as a component in cosmetic and personal care products for its ability to provide a pleasant scent and enhance the overall sensory experience of these products.
Used in Pharmaceutical Industry:
(R)-Methyl 3-Hydroxyoctanoate has potential applications in the pharmaceutical industry, particularly in the development and production of drugs and medical products. Its unique properties make it a valuable compound for research and development in this field.

Upstream product

• 186581-53-3 diazomethane 
• 44987-72-6 (R)-3-hydroxy-octanoic acid 
• 10488-95-6 ethyl 3-oxooctanoate 
• 62344-14-3 (E)-methyl 3-oxo-6-octenoate 
• 105-45-3 acetoacetic acid methyl ester 
• 67-56-1 methanol 
• 22348-95-4 methyl 3-oxooctanoate 
• 13283-91-5 3-oxooctanoic acid 
• 133319-86-5 5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-yl diethyl phosphate 
• 32556-70-0 (R)-1-octyn-3-ol 
• 142-62-1 hexanoic acid 
• 66-25-1 hexanal 
• 108-05-4 vinyl acetate 
• 7367-87-5 3-hydroxyoctanoic acid methyl ester 

Downstream Products

• 44987-72-6 (R)-3-hydroxy-octanoic acid 
• 126442-53-3 (S)-3-hydroxyoctanoic acid benzyl ester 
• 51154-96-2 (R)-massoialactone 
• 115482-38-7 (R)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-octanoic acid methyl ester 

Relevant articles and documents

Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds

A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.87.0 mM and 0.16.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.

Synthesis of enantiopure (R)-(-)-massoialactone through ruthenium-SYNPHOS asymmetric hydrogenation

Total synthesis of enantiopure (R)-(-)-massoialactone was achieved. The key step includes the asymmetric hydrogenation of an achiral β-keto ester using a ruthenium-SYNPHOS catalyst to set the hydroxyl function in a stereocontrolled manner with excellent enantioselectivity (>99% ee). Ring closing metathesis (RCM) in the presence of Grubbs' catalyst allows the final construction of the six-membered lactone.

Optically active compound and process for producing the same

An optically active (2S,3R)-2-(3'-hydroxyacyl)aminoalkane-1,3-diol and a process for producing the same are disclosed. The compound is represented by the following general formula (1): STR1 wherein R1 represents a linear or branched, saturated aliphatic hydrocarbon group having 9 to 19 carbon atoms; R2 represents a linear or branched, saturated aliphatic hydrocarbon group having 1 to 19 carbon atoms; and symbol * means that the carbon atom is an asymmetric carbon atom of the S or R configuration. The optically active compound is a ceramide in which the fatty acid moiety has an optically active hydroxyl group in the 3-position.