10075-11-3

Basic information

• Product Name: 9(R)-HODE
• Synonyms: 9(R)-HODE;9R-HYDROXY-10E,12Z-OCTADECADIENOIC ACID;NPDSHTNEKLQQIJ-WXUVIADPSA-N
• CAS NO: 10075-11-3
• Molecular Formula: C₁₈H₃₂O₃
• Molecular Weight: 296.44
• Mol File: 10075-11-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 416.1±33.0 °C(Predicted)
• Appearance: /
• Density: 0.970±0.06 g/cm3(Predicted)
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: 9(R)-HODE(CAS DataBase Reference)
• NIST Chemistry Reference: 9(R)-HODE(10075-11-3)
• EPA Substance Registry System: 9(R)-HODE(10075-11-3)

Safety Data

• Hazardous Substances Data: 10075-11-3(Hazardous Substances Data)

Upstream product

• 60-33-3 linoleic acid 
• 2420-55-5 linoleic acid 
• 137284-16-3 (E)-9-Acetoxy-11-bromo-undec-10-enoic acid butyl ester 
• 870-09-7 Heleninolsaeure-methylester 
• 137284-31-2 (E)-(R)-11-Bromo-9-hydroxy-undec-10-enoic acid 
• 628-71-7 1-Heptyne 
• 6084-82-8 (R)-9-hydroxy-(10E,12Z)-10,12-octadecadienoic acid methyl ester 

Relevant articles and documents

Stereospecific production of 9R-hydroxy-10E,12Z-octadecadienoic acid from linoleic acid by recombinant Escherichia coli cells expressing 9R-lipoxygenase from Nostoc sp. SAG 25.82

One of the most significant properties of lipoxygenase (LOX) as a biocatalyst is its stereo-selective oxygenation. In this study, the stereo-specific production of 9R-hydroxy-10E,12Z-octadecadienoic acid (9R-HODE) from linoleic acid was achieved using whole recombinant Escherichia coli cells expressing LOX from Nostoc sp. SAG 25.82. The optimal conditions for the production of 9R-HODE were pH 7.5, 25 °C, 40 g l-1 cells, 15 g l-1 linoleic acid, 2% (v/v) methanol, 1 working volume/oxygen volume/min (vvm) oxygenation rate, and 250 rpm agitation speed in 500 ml-baffled flask containing a working volume of 50 ml. Under these optimized conditions, whole recombinant cells expressing 9R-LOX protein produced 14.3 g l-1 9R-HODE for 1 h, with a conversion yield of 95% (w/w) and a productivity of 14.3 g l-1 h-1. The oxygen supply method significantly influenced stereo- and regio-selectivity of the oxygenation of linoleic acid. Among the oxygen supply methods tested, oxygenation (1 vvm) with agitation (250 rpm) resulted in the highest 9R/13S-HODE ratio of the products at 96:4. This is the first application using whole recombinant cells harboring R-specific LOX for the stereo-selective production of an R-specific hydroxy fatty acid.

Lipase Catalysed Regio- and Enantio-selective Hydrolysis: Molecular Recognition Phenomenon and Synthesis of (R)-Dimorphecolic Acid

Molecular recognition has been observed in hydrolysis of racemic esters of (E)-9=acetoxy-11-bromoundec-10-enoic acid by a lipase of Candida cylindracea (E.C. 3.1.1.3) where optically active (R)-(E)-9-acetoxy-11-bromoundec-10-enoic acid 99percent> was obtained which was used in synthesis of (R)-dimorphecolic acid.