WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 581883
CAS#: 5393-81-7
Description: 2-Hydroxydecanoic acid is a fatty acid found in the lipophilic portion of the lipopolysaccharide fraction of P. ovalis, an aerobic bacterium.1 Synthesis of the hydroxy portion of 2-hydroxy decanoic acid occurs through oxygenation by monooxygenase, using molecular O2 as its substrate.
MedKoo Cat#: 581883
Name: 2-Hydroxydecanoic acid
CAS#: 5393-81-7
Chemical Formula: C10H20O3
Exact Mass: 188.1412
Molecular Weight: 188.27
Elemental Analysis: C, 63.80; H, 10.71; O, 25.49
Synonym: 2-Hydroxydecanoic acid; 2-Hydroxydecanoate; alpha-Hydroxydecanoic acid; (±)-2-hydroxy Decanoic Acid; (±)-α-hydroxy Decanoic Acid; 2-hydroxy Decylic Acid; α-hydroxy Decylic Acid; NSC 4801.
IUPAC/Chemical Name: (S)-2-hydroxydecanoic acid
InChi Key: GHPVDCPCKSNJDR-VIFPVBQESA-N
InChi Code: InChI=1S/C10H20O3/c1-2-3-4-5-6-7-8-9(11)10(12)13/h9,11H,2-8H2,1H3,(H,12,13)/t9-/m0/s1
SMILES Code: C([C@@H](C(O)=O)O)CCCCCCC
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 188.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Deshmukh SC, Talukdar P. Stereoselective synthesis of (2S,3R)-α-hydroxy-β-amino acids (AHBAs): valinoctin A, (2S,3R)-3-amino-2-hydroxydecanoic acid, and a fluorescent-labeled (2S,3R)-AHBA. J Org Chem. 2014 Nov 21;79(22):11215-25. doi: 10.1021/jo501751u. Epub 2014 Oct 31. PubMed PMID: 25308171.
2: Rohokale RS, Dhavale DD. Synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and its enantiomer: a non-proteinogenic amino acid segment of the linear pentapeptide microginin. Beilstein J Org Chem. 2014 Mar 17;10:667-71. doi: 10.3762/bjoc.10.59. eCollection 2014. PubMed PMID: 24778718; PubMed Central PMCID: PMC3999816.
3: Tsuji H, Eto T, Sakamoto Y. Synthesis and Hydrolytic Degradation of Substituted Poly(DL-Lactic Acid)s. Materials (Basel). 2011 Aug 10;4(8):1384-1398. doi: 10.3390/ma4081384. PubMed PMID: 28824149; PubMed Central PMCID: PMC5448671.
4: Nagahashi G, Douds DD Jr. The effects of hydroxy fatty acids on the hyphal branching of germinated spores of AM fungi. Fungal Biol. 2011 Apr-May;115(4-5):351-8. doi: 10.1016/j.funbio.2011.01.006. Epub 2011 Feb 1. PubMed PMID: 21530917.
5: Pormsila W, Gong XY, Hauser PC. Determination of the enantiomers of alpha-hydroxy- and alpha-amino acids in capillary electrophoresis with contactless conductivity detection. Electrophoresis. 2010 Jun;31(12):2044-8. doi: 10.1002/elps.201000127. PubMed PMID: 20496346.
6: Das S, Glenn JH 4th, Subramanian M. Enantioselective oxidation of 2-hydroxy carboxylic acids by glycolate oxidase and catalase coexpressed in methylotrophic Pichia pastoris. Biotechnol Prog. 2010 May-Jun;26(3):607-15. doi: 10.1002/btpr.363. PubMed PMID: 20014430.
7: Sano T, Takagi H, Morrison LF, Metcalf JS, Codd GA, Kaya K. Leucine aminopeptidase M inhibitors, cyanostatin A and B, isolated from cyanobacterial water blooms in Scotland. Phytochemistry. 2005 Mar;66(5):543-8. PubMed PMID: 15721946.
8: Wee AG, McLeod DD. Stereoselective synthesis of the nonproteinogenic amino acid (2S,3R)-3-amino-2-hydroxydecanoic acid from (4S,5S)-4-formyl-5-vinyl-2-oxazolidinone. J Org Chem. 2003 Aug 8;68(16):6268-73. PubMed PMID: 12895060.
9: Takahashi K, Murakami T, Kamata A, Yumoto R, Higashi Y, Yata N. Pharmacokinetic analysis of the absorption enhancing action of decanoic acid and its derivatives in rats. Pharm Res. 1994 Mar;11(3):388-92. PubMed PMID: 8008704.
