(±)-myrmicacin
decanoic acid, 3-hydroxy-, (+-)-
Identification
| Name | (±)-myrmicacin |
| CAS Number | 5561-87-5 |
| FDA UNII | Search |
| Molecular Formula | C10 H20 O3 |
| Molecular Weight | 188.26700000 |
| MDL Number | MFCD00133275 |
| Nikkaji Number | J19.953B |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 318.20 °C. @ 760.00 mm Hg (est) |
| Flash Point | 321.00 °F. TCC ( 160.50 °C. ) (est) |
| logP (o/w) | 2.050 (est) |
| Soluble in | water, 3087 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for (±)-myrmicacin usage levels up to | not for fragrance use. |
| Recommendation for (±)-myrmicacin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
decanoic acid, 3-hydroxy-, (+-)-
(±)-3-
hydroxydecanoic acid
PubMed:
Rapid total synthesis of cyclic lipodepsipeptides as a premise to investigate their self-assembly and biological activity.
PubMed:
Direct enantioseparation of underivatized aliphatic 3-hydroxyalkanoic acids with a quinine-based zwitterionic chiral stationary phase.
PubMed:
Total synthesis and anti-hepatitis C virus activity of MA026.
PubMed:
Medium chain length polyhydroxyalkanoate (mcl-PHA) production from volatile fatty acids derived from the anaerobic digestion of grass.
PubMed:
Simultaneous inhibition of rhamnolipid and polyhydroxyalkanoic acid synthesis and biofilm formation in Pseudomonas aeruginosa by 2-bromoalkanoic acids: effect of inhibitor alkyl-chain-length.
PubMed:
Stimulation of adult neural stem cells with a novel glycolipid biosurfactant.
PubMed:
Lipase-catalyzed acylation of microbial mannosylerythritol lipids (biosurfactants) and their characterization.
PubMed:
The anti-cancer activity of a cationic anti-microbial peptide derived from monomers of polyhydroxyalkanoate.
PubMed:
Development of a bioprocess to convert PET derived terephthalic acid and biodiesel derived glycerol to medium chain length polyhydroxyalkanoate.
PubMed:
Functional characterization of an NADPH dependent 2-alkyl-3-ketoalkanoic acid reductase involved in olefin biosynthesis in Stenotrophomonas maltophilia.
PubMed:
Long-chain 3-hydroxy fatty acids accumulating in LCHAD and MTP deficiencies induce oxidative stress in rat brain.
PubMed:
Aureobasidin, new antifouling metabolite from marine-derived fungus Aureobasidium sp.
PubMed:
Up-cycling of PET (polyethylene terephthalate) to the biodegradable plastic PHA (polyhydroxyalkanoate).
PubMed:
The conversion of BTEX compounds by single and defined mixed cultures to medium-chain-length polyhydroxyalkanoate.
PubMed:
Successful treatment of chronic decubitus ulcer with 0.1% dirhamnolipid ointment.
PubMed:
Age-dependent changes in the chemistry of exocrine glands of Bombus terrestris queens.
PubMed:
Pseudomonas japonica sp. nov., a novel species that assimilates straight chain alkylphenols.
PubMed:
Production and characterization of polyhydroxyalkanoates in Pseudomonas aeruginosa ATCC 9027 from glucose, an unrelated carbon source.
PubMed:
Unique lipid a modifications in Pseudomonas aeruginosa isolated from the airways of patients with cystic fibrosis.
PubMed:
Metabolite profiles of lactic acid bacteria in grass silage.
PubMed:
Enhanced healing of full-thickness burn wounds using di-rhamnolipid.
PubMed:
[The structure of uncommon lipid A from the marine bacterium Marinomonas communis ATCC 27118T].
PubMed:
Biosynthesis of medium chain length poly(3-hydroxyalkanoates) (mcl-PHAs) by Comamonas testosteroni during cultivation on vegetable oils.
PubMed:
Synthesis of short-/medium-chain-length poly(hydroxyalkanoate) blends by mixed culture fermentation of glycerol.
PubMed:
Biosynthetic pathway of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines.
PubMed:
Structural characterization of lipid A from nontypeable and type f Haemophilus influenzae: variability of fatty acid substitution.
PubMed:
Microbial production and applications of chiral hydroxyalkanoates.
PubMed:
Thioesterase II of Escherichia coli plays an important role in 3-hydroxydecanoic acid production.
PubMed:
Detailed structure of lipid A isolated from lipopolysaccharide from the marine proteobacterium Marinomonas vaga ATCC 27119.
PubMed:
Structure of lipid A from the marine gamma-proteobacterium Marinomonas vaga ATCC 27119T lipopolysaccharide.
PubMed:
Pseudomonas lutea sp. nov., a novel phosphate-solubilizing bacterium isolated from the rhizosphere of grasses.
PubMed:
Production of 3-hydroxydecanoic acid by recombinant Escherichia coli HB101 harboring phaG gene.
PubMed:
Pseudomonas rhizosphaerae sp. nov., a novel species that actively solubilizes phosphate in vitro.
PubMed:
First-order kinetics analysis of monomer composition dependent polyhydroxyalkanoic acid degradation in Pseudomonas spp.
PubMed:
Production of D-(--)-3-hydroxyalkanoic acid by recombinant Escherichia coli.
PubMed:
Physiological characterization and genetic engineering of Pseudomonas corrugata for medium-chain-length polyhydroxyalkanoates synthesis from triacylglycerols.
PubMed:
Endotoxic properties of lipid A from Comamonas testosteroni.
PubMed:
Highly regioselective Vilsmeier-Haack acylation of hexahydropyrroloindolizine.
PubMed:
Configurational analysis of chiral acids as O-trifluoroacetylated (-)-menthyl esters by achiral dual-capillary column gas chromatography.
PubMed:
In vitro synthesis of poly(3-hydroxydecanoate): purification and enzymatic characterization of type II polyhydroxyalkanoate synthases PhaC1 and PhaC2 from Pseudomonas aeruginosa.
PubMed:
Description of strain 3CB-1, a genomovar of Thauera aromatica, capable of degrading 3-chlorobenzoate coupled to nitrate reduction.
PubMed:
Production of polyhydroxyalkanoic acids by Ralstonia eutropha and Pseudomonas oleovorans from an oil remaining from biotechnological rhamnose production.
PubMed:
Increased flow of fatty acids toward beta-oxidation in developing seeds of Arabidopsis deficient in diacylglycerol acyltransferase activity or synthesizing medium-chain-length fatty acids.
PubMed:
Liquid chromatography/mass spectrometry analysis of mixtures of rhamnolipids produced by Pseudomonas aeruginosa strain 57RP grown on mannitol or naphthalene.
PubMed:
Outer membrane changes in a toluene-sensitive mutant of toluene-tolerant Pseudomonas putida IH-2000.
PubMed:
Corpeptins, new bioactive lipodepsipeptides from cultures of Pseudomonas corrugata.
PubMed:
Pholipeptin, a Novel Cyclic Lipoundecapeptide fromPseudomonas fluorescens.
PubMed:
Chemistry of metapleural gland secretions of three attine ants,Atta sexdens rubropilosa, Atta cephalotes, andAcromyrmex octospinosus (Hymenoptera: Formicidae).
PubMed:
Chemical structure of lipid A isolated from Comamonas testosteroni lipopolysaccharide.
PubMed:
Lipopolysaccharide and porin of Roseobacter denitrificans, confirming its phylogenetic relationship to the alpha-3 subgroup of Proteobacteria.
PubMed:
Pharmacokinetic analysis of the absorption enhancing action of decanoic acid and its derivatives in rats.
PubMed:
Isoprenoid quinones and fatty acids of Zoogloea.
PubMed:
A novel extracellular cyclic lipopeptide which promotes flagellum-dependent and -independent spreading growth of Serratia marcescens.
PubMed:
Structural characterization of the lipid A component of Pseudomonas aeruginosa wild-type and rough mutant lipopolysaccharides.
PubMed:
Fatty acid alterations and polymyxin B binding by lipopolysaccharides from Pseudomonas aeruginosa adapted to polymyxin B resistance.
PubMed:
Structural analysis of the nontoxic lipid A of Rhodobacter capsulatus 37b4.
PubMed:
beta-Hydroxydecanoylthioester dehydrase: a rapid, convenient, and accurate product distribution assay.
PubMed:
Structural studies on the non-toxic lipid A from Rhodopseudomonas sphaeroides ATCC 17023.
PubMed:
Nontoxic lipopolysaccharide from Rhodopseudomonas sphaeroides ATCC 17023.
PubMed:
Shape-transforming action of myrmicacin (3-hydroxydecanoic acid) and some related compounds on the membrane of intact human erythrocytes.
PubMed:
Structural studies on the D-arabinose-containing lipid A from Rhodospirillum tenue 2761.
PubMed:
Myrmicacin, a new inhibitor for mitotic progression after metaphase.
PubMed:
Studies of lipid A fractions from the lipopolysaccharides of Pseudomonas aeruginosa and Pseudomonas alcaligenes.
PubMed:
Myrmicacin, the first insect herbicide.
PubMed:
The purification and chemical composition of the lipopolysaccharide of Pseudomonas alcaligenes.
PubMed:
The chemical composition of the lipopolyacarideof Pseudomonas aeruginosa.
PubMed:
Novel fatty acids from the royal jelly of honeybees (Apis mellifera, L.).