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379700 Aldrich

10-Hydroxydecanoic acid

technical grade

Synonym: NSC 15139

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Properties

Related Categories Biochemicals and Reagents, Building Blocks, C10, Carbonyl Compounds, Carboxylic Acids,
grade   technical grade
impurities   <15% intermolecular dilactone
mp   75-77 °C(lit.)

Description

Packaging

5 g in glass bottle

500 mg in poly bottle

Application

10-Hydroxydecanoic acid is suitable for use in a study on Novozym 435-catalyzed condensation polymerization of cis-9,10-epoxy-18-hydroxyoctadecanoic acid and its comparison with corresponding polymerization of 10-hydroxydecanoic acid.1

Reactant involved in:
• Synthesis of copolymers of acrylamide and sodium acryloyloxydecanoate
• Macrolactonization for preparation of Sansalvamide A
• Studies of chain length selectivity for cutinase catalyzed polycondensation reactions
• Ruthenium-catalyzed esterification followed by macrocyclization
• Synthesis of anhydrides and esters

General description

10-Hydroxydecanoic acid (10-HDA) is a saturated fatty acid of hydroxy-trans-2-decenoic acid (10H2DA).2 Its molecule has two functional groups (-OH and -COOH).3 It has been reported to prevent the lipopolysaccharide-induced NO production in murine macrophages.2 10-HDA has been extracted from royal jelly obtained from honeybees (Apis mellifera) and exhibits estrogenic action.4, Its polymerization with the polyethylene glycol-modified lipase in a transparent benzene solution has been reported to proceed by the formation of ester linkage.3

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Safety & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

MSMLS Online Plate Map

MSMLS compounds are conveniently provided at 5μg per well, enough for multiple injections. These are high purity (>95%) compounds supplied in an economical, ready to use format. Compounds are arrange...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers

References

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1. Lipase-catalyzed synthesis of an epoxy-functionalized polyester from the suberin monomer cis-9,10-epoxy-18-hydroxyoctadecanoic acid. Olsson A, Lindström M, and Iversen T Biomacromolecules 8(2), 757-60, (2007)

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2. Inhibitory effect of 10-hydroxydecanoic acid on lipopolysaccharide-induced nitric oxide production via translational downregulation of interferon regulatory factor-1 in RAW264 murine macrophages. Takahashi K, Sugiyama T, Tokoro S, et al. Biomed. Res. 34(4), 205-14, (2013)

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3. Polymerization of 10-hydroxydecanoic acid in benzene with polyethylene glycol-modified lipase. Ajima A, et al. Biotechnol. Lett. 7(5), 303-306, (1985)

4. Estrogenic activities of Fatty acids and a sterol isolated from royal jelly. Suzuki KM, Isohama Y, Maruyama H, et al. Evid. Based. Complement. Alternat. Med. 5(3), 295-302, (2008)

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Exploring Chain Length Selectivity in HIC-Catalyzed Polycondensation Reactions D. Feder and R. A. Gross, Biomacromolecules 11, 690-697, (2010)

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A highly efficient macrolactonization method via ethoxyvinyl ester Y. Ohba, et al., Chemistry 15, 3526-3537, (2009)

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Synthesis, characterization, and aqueous solution behavior of copolymers of acrylamide and sodium 10-acryloyloxydecanoate C. Song, et al., Polymer Bull. 67, 1917-1934, (2011)

Reaction of dicarbonates with carboxylic acids catalyzed by weak lewis acids: general method for the synthesis of anhydrides and esters G. Bartoli, et al., Synthesis 22, 3489-3496, (2007)

Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: synthesis of Sansalvamide A J. A. Morales-Serna, et al., Org. Biomol. Chem. 8, 4940-4948, (2010)

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Beil. 3,II,242

FT-NMR 1 (1), 810:B / RegBook 1 (1), 567:C / Structure Index 1, 81:A:2

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