1883-13-2

Basic information

• Product Name: 3-HYDROXYDODECANOIC ACID
• Synonyms: 3-HYDROXY C12:0 ACID;(+/-)-3-HYDROXYDODECANOIC ACID;3-HYDROXYDODECANOIC ACID;DL-BETA-HYDROXYLAURIC ACID;3-Hydroxydodecanoic acid, 98 %
• CAS NO: 1883-13-2
• Molecular Formula: C₁₂H₂₄O₃
• Molecular Weight: 216.32
• Product Categories: Acyclics, Miscellaneous Reagents
• Mol File: 1883-13-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 70-70.5 °C
• Boiling Point: 348 °C at 760 mmHg
• Flash Point: 178.4 °C
• Appearance: /
• Density: 0.987 g/cm³
• Vapor Pressure: 5.86E-10mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.38±0.10(Predicted)
• CAS DataBase Reference: 3-HYDROXYDODECANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYDODECANOIC ACID(1883-13-2)
• EPA Substance Registry System: 3-HYDROXYDODECANOIC ACID(1883-13-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 1883-13-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1883-13-2 differently. You can refer to the following data:
1. 3-hydroxydodecanoic acid is used in the study of Lipid A, a major constituent of the lipopolysaccharides, which are responsible for the toxicity of gram negative bacteria. Also used in the synthesis of olefins from β-hydroxy carboxylic acids.
2. 3-Hydroxylauric Acid is used in the study of Lipid A, a major constituent of the lipopolysaccharides, which are responsible for the toxicity of gram negative bacteria. Also used in the synthesis of olefins from β-hydroxy carboxylic acids.

Definition

ChEBI: A medium-chain fatty acid that is the 3-hydroxylated derivative of lauric acid; associated with fatty acid metabolic disorders.

Biochem/physiol Actions

DL-3-Hydroxydodecanoic acid (3HDD) is a racemic mixture of D- and L-3HDD. 3-hydroxydodecanoic acid is found as a monomer in the construction of polyhydroxyalkanoates. 3HDD is used to study the roles of β-hydroxy fatty acids in chronic inflammation and insulin resistance and the biosynthesis of diffusible signal factors involved in quorum sensing.

InChI:InChI=1/C19H28O3/c1-18-6-5-15-14(16(18)8-13(21)10-18)4-3-11-7-12(20)9-17(22)19(11,15)2/h9,11,13-16,20-21H,3-8,10H2,1-2H3/t11?,13?,14-,15+,16+,18-,19+/m1/s1

Upstream product

• 112-31-2 caprinaldehyde 
• 96-32-2 bromoacetic acid methyl ester 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 142-61-0 Hexanoyl chloride 
• 933486-31-8 C₁₂H₂₄O₂ 
• 117951-87-8 1-tridecen-4-ol 
• 111-83-1 1-bromo-octane 
• 67342-99-8 ethyl 3-oxododecanoate 
• 143-07-7 lauric acid 
• 112-13-0 n-decanoyl chloride 
• 183613-15-2 3-hydroxydodecanoic acid ethyl ester 
• 61058-75-1 3-oxo-dodecanoic acid 
• 72864-23-4 β-hydroxydodecanoic acid methyl ester 
• 5292-43-3 bromoacetic acid tert-butyl ester 

Downstream Products

• 72864-23-4 β-hydroxydodecanoic acid methyl ester 
• 53941-37-0 benzyl 3-hydroxydodecanoate 
• 182359-60-0 N-(3-hydroxy-dodecanoyl)-L-homoserine lactone 
• 124710-51-6 2-Tetradecyl-hexadecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-3-(3-hydroxy-dodecanoylamino)-tetrahydro-pyran-4-yl ester 
• 19009-56-4 2-methyldecanal 

Relevant articles and documents

Structure of the unusual Sinorhizobium fredii HH103 lipopolysaccharide and its role in symbiosis

Rhizobia are soil bacteria that form important symbiotic associations with legumes, and rhizobial surface polysaccharides, such as K-antigen polysaccharide (KPS) and lipopolysaccharide (LPS), might be important for symbiosis. Previously, we obtained a mutant of Sinorhizobium fredii HH103, rkpA, that does not produce KPS, a homopolysaccharide of a pseudaminic acid derivative, but whose LPS electrophoretic profile was indistinguishable from that of the WT strain. We also previously demonstrated that the HH103 rkpLMNOPQ operon is responsible for 5-acetamido-3,5,7,9-tetradeoxy-7-(3-hydroxybutyramido)-L-glyc-ero-L-manno-nonulosonic acid [Pse5NAc7(3OHBu)] production and is involved in HH103 KPS and LPS biosynthesis and that an HH103 rkpM mutant cannot produce KPS and displays an altered LPS structure. Here, we analyzed the LPS structure of HH103 rkpA, focusing on the carbohydrate portion, and found that it contains a highly heterogeneous lipid A and a peculiar core oligosaccharide composed of an unusually high number of hexuronic acids containing b-configured Pse5NAc7(3OHBu). This pseudaminic acid derivative, in its a-configuration, was the only structural component of the S. fredii HH103 KPS and, to the best of our knowledge, has never been reported from any other rhizobial LPS. We also show that Pse5NAc7(3OHBu) is the complete or partial epitope for a mAb, NB6-228.22, that can recognize the HH103 LPS, but not those of most of the S. fredii strains tested here. We also show that the LPS from HH103 rkpM is identical to that of HH103 rkpA but devoid of any Pse5NAc7(3OHBu) residues. Notably, this rkpM mutant was severely impaired in symbiosis with its host, Macroptilium atropurpureum.

Succinct synthesis of saturated hydroxy fatty acids and: In vitro evaluation of all hydroxylauric acids on FFA1, FFA4 and GPR84

Saturated hydroxy fatty acids make up a class of underexplored lipids with potentially interesting biological activities. We report a succinct and general synthetic route to saturated hydroxy fatty acids hydroxylated at position 6 or higher, and exemplify this with the synthesis of hydroxylauric acids. All regioisomers of hydroxylauric acids were tested on free fatty acid receptors FFA1, FFA4 and GPR84. The results show that the introduction of a hydroxy group and its position have a high impact on receptor activity.

Erratum: A Continuous, Fluorogenic Sirtuin 2 Deacylase Assay: Substrate Screening and Inhibitor Evaluation (Journal of Medicinal Chemistry (2016) 59 (1021-1031) DOI 10.1021/acs.jmedchem.5b01532)

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