141-23-1

Basic information

• Product Name: METHYL 12-HYDROXYSTEARATE
• Synonyms: 12-hydroxy-octadecanoicacimethylester;12-hydroxy-stearicacimethylester;cenwaxme;kemester1288;methylhydroxystearate;Octadecanoicacid,12-hydroxy-,methylester;DL-12-HYDROXYSTEARIC ACID METHYL ESTER;METHYL 12-HYDROXYOCTADECANOATE
• CAS NO: 141-23-1
• Molecular Formula: C₁₉H₃₈O₃
• Molecular Weight: 314.5
• EINECS: 205-471-8
• Mol File: 141-23-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 53.5°C
• Boiling Point: 394.16°C (rough estimate)
• Flash Point: 147.6 °C
• Appearance: /
• Density: 1.0196 (rough estimate)
• Vapor Pressure: 4.63E-08mmHg at 25°C
• Refractive Index: 1.4410 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.40±0.20(Predicted)
• Water Solubility: 89.94μg/L at 25℃
• CAS DataBase Reference: METHYL 12-HYDROXYSTEARATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 12-HYDROXYSTEARATE(141-23-1)
• EPA Substance Registry System: METHYL 12-HYDROXYSTEARATE(141-23-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 141-23-1(Hazardous Substances Data)

Usage

Description

METHYL 12-HYDROXYSTEARATE, also known as Methyl 12-hydroxy stearate, is a fatty acid ester derived from the esterification of 12-Hydroxy stearic acid with methanol. It is a white, waxy solid that can be found in both solid and liquid forms. METHYL 12-HYDROXYSTEARATE is characterized by its high melting point, low acid value, and limited solubility in organic solvents. It is combustible and has various applications across different industries due to its unique chemical properties.

Uses

Used in Adhesives:
METHYL 12-HYDROXYSTEARATE is used as an additive in the adhesives industry to improve the adhesive's performance, such as increasing its drop points and enhancing its oxidative stability.
Used in Inks:
In the inks industry, METHYL 12-HYDROXYSTEARATE is utilized as a component to enhance the ink's properties, including its stability and resistance to bleeding.
Used in Cosmetics:
METHYL 12-HYDROXYSTEARATE is employed as an ingredient in the cosmetics industry for its emollient and skin-conditioning properties, contributing to the product's texture and feel.
Used in Greases:
METHYL 12-HYDROXYSTEARATE is used as a base oil in the continuous grease process, where it helps formulate greases with higher drop points, reduced bleeding, and improved oxidative stability.
Used in Textile Ancillary:
In the textile industry, METHYL 12-HYDROXYSTEARATE is used as a component in textile ancillary products, enhancing their performance and quality.
Used in Paper Industry:
METHYL 12-HYDROXYSTEARATE is utilized in the paper industry to improve the properties of paper products, such as their strength and durability.
Used in Sphingomyelin Research:
METHYL 12-HYDROXYSTEARATE is used as a fatty acid reagent in the study of sphingomyelin through site-specific deuterium labeling, contributing to the understanding of its structure and function.
Used in Lipoconjugate Preparation:
METHYL 12-HYDROXYSTEARATE is employed in the preparation of ricinoleate-based lipoconjugates of phenolic acids, which possess antioxidant and antifungal properties, for various applications in the pharmaceutical and chemical industries.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C19H38O3/c1-3-4-5-12-15-18(20)16-13-10-8-6-7-9-11-14-17-19(21)22-2/h18,20H,3-17H2,1-2H3/t18-/m1/s1

Upstream product

• 23224-20-6 methyl ricinoleate 
• 41989-07-5 methyl ricinoleate 
• 111-70-6 n-heptan1ol 
• 111-81-9 Methyl 10-undecenoate 
• 67-56-1 methanol 
• 106-14-9 12-Hydroxystearic acid 
• 67529-83-3 (E)-methyl 12-hydroxy-9-octadecenoate 
• 5417-30-1 12-hydroxy-octadecanoic acid butyl ester 
• 6198-58-9 methyl (Z)-vaccenate 
• 2528-61-2 Heptanoic acid chloride 
• 95080-06-1 12-Oxo-octadec-10-ynoic acid methyl ester 
• 95080-08-3 methyl 12-hydroxyoctadec-10-ynoate 
• 95189-43-8 12-hydroxyoctadec-trans-10-enoic acid 
• 95080-07-2 12-hydroxyoctadec-10-ynoic acid 

Downstream Products

• 106-14-9 12-Hydroxystearic acid 
• 1852-04-6 undecanedioic acid 
• 67123-61-9 12-(4'-nitro-4-dimethylaminoazobenzene-3'-carboxyloxy)stearic acid 
• 73640-24-1 12-(4'-nitro-4-dimethylaminostilbene-3'-carbonyloxy)stearic acid 
• 1731-79-9 dodecanedioic acid dimethyl ester 
• 1383325-24-3 methyl 12-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]octadecanoate 
• 1383325-25-4 methyl 12-(4-hydroxy-3-methoxybenzoyloxy)octadecan-1-oate 
• 1423018-62-5 (3-((12-imidazol-1-yl)-octadecanoyl)propyl)triphenylphosphonium bromide 
• 1037310-43-2 methyl 12-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)octadecanoate 

Relevant articles and documents

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Photochemistry of parathion in the plant cuticle environment: Model reactions in the presence of 2-propanol and methyl 12-hydroxystearate

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Attempted Synthesis of (9Z)-Methyl 12-Hydroperoxyoctadec-9-enoate

The silver trifluoroacetate-assisted reaction of alkyl halides with hydrogen peroxide has been investigated.Methyl 12-bromostearate furnished, for the first time, methyl 12-hydroperoxystearate in 34percent yield.Methyl 12-bromo-oleate, however, gave cyclopropane hydroperoxides (via a homoallylic cation rearrangement) and hydroperoxy epidioxides (presumably via methyl 12-hydroperoxyoleate which could not be isolated).Methyl 9-t-butylperoxy-10,11-methyleneheptadecanoate was produced by the reaction of methyl 12-bromo-oleate with t-butyl hydroperoxide in the presence of silver trifluoroacetate.None of these transformations occurred when silver trifluoroacetate was replaced by the acetate.

Uncovering potential interspecies signaling factors in plant-derived mixed microbial culture

Microbes use signaling factors for intraspecies and interspecies communications. While many intraspecies signaling factors have been found and characterized, discovery of factors for interspecies communication is lagging behind. To facilitate the discovery of such factors, we explored the potential of a mixed microbial culture (MMC) derived from wheatgrass, in which heterogeneity of this microbial community might elicit signaling factors for interspecies communication. The stability of Wheatgrass MMC in terms of community structure and metabolic output was first characterized by 16S ribosomal RNA amplicon sequencing and liquid chromatography/mass spectrometry (LC/MS), respectively. In addition, detailed MS analyses led to the identification of 12-hydroxystearic acid (12-HSA) as one of the major metabolites produced by Wheatgrass MMC. Stereochemical analysis revealed that Wheatgrass MMC produces mostly the (R)-isomer, although a small amount of the (S)-isomer was also observed. Furthermore, 12-HSA was found to modulate planktonic growth and biofilm formation of various marine bacterial strains. The current study suggests that naturally derived MMCs could serve as a simple and reproducible platform to discover potential signaling factors for interspecies communication. In addition, the study indicates that hydroxylated long-chain fatty acids, such as 12-HSA, may constitute a new class of interspecies signaling factors.

A Bi-Enzymatic Cascade Pathway towards Optically Pure FAHFAs**

Recently discovered endogenous mammalian lipids, fatty acid esters of hydroxy fatty acids (FAHFAs), have been proved to have anti-inflammatory and anti-diabetic effects. Due to their extremely low abundancies in vivo, forging a feasible scenario for FAHFA synthesis is critical for their use in uncovering biological mechanisms or in clinical trials. Here, we showcase a fully enzymatic approach, a novel in vitro bi-enzymatic cascade system, enabling an effective conversion of nature-abundant fatty acids into FAHFAs. Two hydratases from Lactobacillus acidophilus were used for converting unsaturated fatty acids to various enantiomeric hydroxy fatty acids, followed by esterification with another fatty acid catalyzed by Candida antarctica lipase A (CALA). Various FAHFAs were synthesized in a semi-preparative scale using this bi-enzymatic approach in a one-pot two-step operation mode. In all, we demonstrate that the hydratase-CALA system offers a promising route for the synthesis of optically pure structure-diverse FAHFAs.

Use of esters or amides of hydroxylated carboxylic acids as solubilizers

The use of esters or amides of hydroxylated carboxylic acids as solubilizers, particularly for pharmaceutical, cosmetic and food preparations, is described.