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379700

Sigma-Aldrich

10-Hydroxydecanoic acid

technical grade

Synonym(s):
NSC 15139
Linear Formula:
HO(CH2)9CO2H
CAS Number:
Molecular Weight:
188.26
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

impurities

<15% intermolecular dilactone

mp

75-77 °C (lit.)

SMILES string

OCCCCCCCCCC(O)=O

InChI

1S/C10H20O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h11H,1-9H2,(H,12,13)

InChI key

YJCJVMMDTBEITC-UHFFFAOYSA-N

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General description

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

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.
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

Packaging

5 g in glass bottle
500 mg in glass insert

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Keita Takahashi et al.
Biomedical research (Tokyo, Japan), 34(4), 205-214 (2013-09-03)
Toll-like receptors (TLRs) play a critical role in innate immunity by recognizing pathogen-associated molecular patterns. Various environmental materials including lipids may affect TLR signaling and modulate innate immune responses. We previously reported that 10-hydroxy-trans-2-decenoic acid (10H2DA) inhibits lipopolysaccharide (LPS)-induced interleukin...
Martin T Gaugg et al.
Journal of breath research, 11(4), 046004-046004 (2017-09-14)
We explore whether real-time breath analysis by high resolution mass spectrometry is suitable to monitor changes at the metabolic level due to inhaling bronchodilator medication. We compared the breath levels of metabolites in a group of patients (n = 50) at baseline...
Polymerization of 10-hydroxydecanoic acid in benzene with polyethylene glycol-modified lipase.
Ajima A, et al.
Biotechnology Letters, 7(5), 303-306 (1985)
Kazu-Michi Suzuki et al.
Evidence-based complementary and alternative medicine : eCAM, 5(3), 295-302 (2008-10-03)
We have previously reported that royal jelly (RJ) from honeybees (Apis mellifera) has weak estrogenic activity mediated by interaction with estrogen receptors that leads to changes in gene expression and cell proliferation. In this study, we isolated four compounds from...
Lipase-catalyzed synthesis of an epoxy-functionalized polyester from the suberin monomer cis-9,10-epoxy-18-hydroxyoctadecanoic acid.
Ann Olsson et al.
Biomacromolecules, 8(2), 757-760 (2007-01-25)

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