73891-08-4

Basic information

• Product Name: (12Z)-9-Hydroxy-12-octadecenoic acid
• Synonyms: (12Z)-9-Hydroxy-12-octadecenoic acid;(Z)-9-Hydroxy-12-octadecenoic acid;Isoricinoleic acid
• CAS NO: 73891-08-4
• Molecular Formula: C₁₈H₃₄O₃
• Molecular Weight: 298.46
• Mol File: 73891-08-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (12Z)-9-Hydroxy-12-octadecenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (12Z)-9-Hydroxy-12-octadecenoic acid(73891-08-4)
• EPA Substance Registry System: (12Z)-9-Hydroxy-12-octadecenoic acid(73891-08-4)

Safety Data

• Hazardous Substances Data: 73891-08-4(Hazardous Substances Data)

Usage

General Description

(12Z)-9-Hydroxy-12-octadecenoic acid, also known as Ricinoleic acid, is a monounsaturated omega-9 fatty acid found in castor oil. It is classified as a hydroxy fatty acid due to the presence of a hydroxyl group on the ninth carbon of the fatty acid chain. Ricinoleic acid is known for its emollient and moisturizing properties, making it a common ingredient in cosmetic and personal care products. It also has anti-inflammatory and antimicrobial properties, which may contribute to its potential therapeutic benefits for skin and hair health. Additionally, ricinoleic acid is used in the production of various industrial products, such as lubricants, plastics, and coatings.

Upstream product

• 60-33-3 linoleic acid 
• 26806-10-0 9(S)-HODE 

Downstream Products

• 1293967-58-4 C₂₄H₃₉NO₃ 
• 1293967-66-4 1-[(9R,12Z)-9-hydroxyoctadec-12-enoyl]-1,3-dicyclohexylurea 

Relevant articles and documents

Hydrogen tunneling steps in cyclooxygenase-2 catalysis

Cyclooxygenases-1 and -2 are tyrosyl radical (Y?)-utilizing hemoproteins responsible for the biosynthesis of lipid-derived autocoids. COX-2, in particular, is a primary mediator of inflammation and believed to be up-regulated in many forms of cancer. Described here are first-of-a-kind studies of COX-2-catalyzed oxidation of the substrate analogue linoleic acid. Very large (≥20) temperature-independent deuterium kinetic isotope effects (KIEs) on the rate constant for enzyme turnover were observed, due to hydrogen atom abstraction from the bisallylic C-H(D) of the fatty acid. The magnitude of the KIE depends on the O2 concentration, consistent with reversible H/D tunneling mediated by the catalytic Y?. At physiological levels of O 2, retention of the hydrogen initially abstracted by the catalytic tyrosine results in strongly temperature-dependent KIEs on O-H(D) homolysis, also characteristic of nuclear tunneling.