DOD | CAS#131021-99-3 | Oleic acid metabolite

MedKoo Cat#: 463974 | Name: DOD

Description:

WARNING: This product is for research use only, not for human or veterinary use.

7,10-dihydroxy-8(E)-Octadecenoic acid (DOD) is a hydroxy fatty acid and metabolite of oleic acid that is produced by P. aeruginosa from vegetable oils. It is active against the food-borne pathogenic bacteria S. aureus, S. typhimurium, L. monocytogenes, B. subtilis, and E. coli, as well as the plant pathogenic bacteria Erwinia, R. solanacearum, C. glutamicum, and P. syringae.

Chemical Structure

DOD

CAS#131021-99-3

Theoretical Analysis

MedKoo Cat#: 463974

Name: DOD

CAS#: 131021-99-3

Chemical Formula: C18H34O4

Exact Mass: 314.2457

Molecular Weight: 314.47

Elemental Analysis: C, 68.75; H, 10.90; O, 20.35

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Synonym

DOD; 7,10-dihydroxy-8(E)-Octadecenoic Acid;

IUPAC/Chemical Name

(E)-7,10-dihydroxyoctadec-8-enoic acid

InChi Key

IPRLELFMTNDNMN-CCEZHUSRSA-N

InChi Code

InChI=1S/C18H34O4/c1-2-3-4-5-6-8-11-16(19)14-15-17(20)12-9-7-10-13-18(21)22/h14-17,19-20H,2-13H2,1H3,(H,21,22)/b15-14+

SMILES Code

CCCCCCCCC(/C=C/C(CCCCCC(O)=O)O)O

Appearance

Solid powder

Purity

>95% (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

>2 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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 314.47 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: Lee YJ, Moon JS, Kim IH, Kim HR. Production of 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid by Pseudomonas aeruginosa KNU-2B. Biotechnol Lett. 2020 Aug;42(8):1547-1558. doi: 10.1007/s10529-020-02883-4. Epub 2020 Apr 3. PMID: 32246345. 2: Chen KY, Kim IH, Hou CT, Watanabe Y, Kim HR. Monoacylglycerol of 7,10-Dihydroxy-8(E)-octadecenoic Acid Enhances Antibacterial Activities against Food-Borne Bacteria. J Agric Food Chem. 2019 Jul 24;67(29):8191-8196. doi: 10.1021/acs.jafc.9b03063. Epub 2019 Jul 11. PMID: 31282662. 3: Tran TK, Kumar P, Kim HR, Hou CT, Kim BS. Microbial Conversion of Vegetable Oil to Hydroxy Fatty Acid and Its Application to Bio-Based Polyurethane Synthesis. Polymers (Basel). 2018 Aug 19;10(8):927. doi: 10.3390/polym10080927. PMID: 30960852; PMCID: PMC6403947. 4: Sohn HR, Bae JH, Hou CT, Kim HR. Antibacterial activity of a 7,10-dihydroxy-8(E)-octadecenoic acid against plant pathogenic bacteria. Enzyme Microb Technol. 2013 Aug 15;53(3):152-3. doi: 10.1016/j.enzmictec.2013.02.009. Epub 2013 Mar 19. PMID: 23830454. 5: Ellamar JB, Song KS, Kim HR. One-step production of a biologically active novel furan fatty acid from 7,10-dihydroxy-8(E)-octadecenoic acid. J Agric Food Chem. 2011 Aug 10;59(15):8175-9. doi: 10.1021/jf2015683. Epub 2011 Jul 7. PMID: 21711016. 6: Suh MJ, Baek KY, Kim BS, Hou CT, Kim HR. Production of 7,10-dihydroxy-8(E)-octadecenoic acid from olive oil by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol. 2011 Mar;89(6):1721-7. doi: 10.1007/s00253-010-3040-2. Epub 2010 Dec 14. PMID: 21153811. 7: Paul S, Hou CT, Kang SC. alpha-Glucosidase inhibitory activities of 10-hydroxy-8(E)-octadecenoic acid: an intermediate of bioconversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid. N Biotechnol. 2010 Sep 30;27(4):419-23. doi: 10.1016/j.nbt.2010.04.002. Epub 2010 Apr 10. PMID: 20385262. 8: Nilsson T, Martínez E, Manresa A, Oliw EH. Liquid chromatography/tandem mass spectrometric analysis of 7,10-dihydroxyoctadecenoic acid, its isotopomers, and other 7,10-dihydroxy fatty acids formed by Pseudomonas aeruginosa 42A2. Rapid Commun Mass Spectrom. 2010 Mar;24(6):777-83. doi: 10.1002/rcm.4446. PMID: 20187080. 9: Khare SK, Kumar A, Kuo TM. Lipase-catalyzed production of a bioactive fatty amide derivative of 7,10-dihydroxy-8(E)-octadecenoic acid. Bioresour Technol. 2009 Feb;100(3):1482-5. doi: 10.1016/j.biortech.2008.08.011. Epub 2008 Sep 14. PMID: 18793843. 10: Kuo TM, Huang JK, Labeda D, Wen L, Knothe G. Production of 10-hydroxy-8(E)-octadecenoic acid from oleic acid conversion by strains of Pseudomonas aeruginosa. Curr Microbiol. 2008 Nov;57(5):437-41. doi: 10.1007/s00284-008-9226-5. Epub 2008 Aug 14. PMID: 18704576. 11: Hou CT. New bioactive fatty acids. Asia Pac J Clin Nutr. 2008;17 Suppl 1:192-5. PMID: 18296335. 12: Chang IA, Bae JH, Suh MJ, Kim IH, Hou CT, Kim HR. Environmental optimization for bioconversion of triolein into 7,10-dihydroxy-8(E)-octadecenoic acid by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol. 2008 Mar;78(4):581-6. doi: 10.1007/s00253-007-1342-9. Epub 2008 Jan 22. PMID: 18210104. 13: Levinson WE, Kuo TM, Knothe G. Characterization of fatty amides produced by lipase-catalyzed amidation of multi-hydroxylated fatty acids. Bioresour Technol. 2008 May;99(7):2706-9. doi: 10.1016/j.biortech.2007.04.058. Epub 2007 Jun 19. PMID: 17582762. 14: Bae JH, Kim DS, Suh MJ, Oh SR, Lee IJ, Kang SC, Hou CT, Kim HR. Production and identification of a novel compound, 7,10-dihydroxy-8(E)-hexadecenoic acid from palmitoleic acid by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol. 2007 May;75(2):435-40. doi: 10.1007/s00253-006-0832-5. Epub 2007 Jan 30. PMID: 17262210. 15: Chang IA, Kim IH, Kang SC, Hou CT, Kim HR. Production of 7, 10-dihydroxy-8(E)-octadecenoic acid from triolein via lipase induction by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol. 2007 Feb;74(2):301-6. doi: 10.1007/s00253-006-0662-5. Epub 2006 Nov 3. PMID: 17082930. 16: Kuo TM, Nakamura LK. Diversity of oleic acid, ricinoleic acid and linoleic acid conversions among Pseudomonas aeruginosa strains. Curr Microbiol. 2004 Oct;49(4):261-6. doi: 10.1007/s00284-004-4296-5. PMID: 15386114. 17: Busquets M, Deroncelé V, Vidal-Mas J, Rodríguez E, Guerrero A, Manresa A. Isolation and characterization of a lipoxygenase from Pseudomonas 42A2 responsible for the biotransformation of oleic acid into ( S )-( E )-10-hydroxy-8-octadecenoic acid. Antonie Van Leeuwenhoek. 2004 Feb;85(2):129-39. doi: 10.1023/B:ANTO.0000020152.15440.65. Erratum in: Antonie Van Leeuwenhoek. 2004 Aug;86(2):201. PMID: 15028873. 18: Kuo TM, Lanser AC. Factors influencing the production of a novel compound, 7,10-dihydroxy-8(E)-octadecenoic acid, by Pseudomonas aeruginosa PR3 (NRRL B-18602) in batch cultures. Curr Microbiol. 2003 Sep;47(3):186-91. doi: 10.1007/s00284-002-3983-3. PMID: 14570267. 19: Kuo TM, Ray KJ, Manthey LK. A facile reactor process for producing 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid conversion by Pseudomonas aeruginosa. Biotechnol Lett. 2003 Jan;25(1):29-33. doi: 10.1023/a:1021765727998. PMID: 12882302. 20: Guerrero A, Casals I, Busquets M, Leon Y, Manresa A. Oxydation of oleic acid to (E)-10-hydroperoxy-8-octadecenoic and (E)-10-hydroxy-8-octadecenoic acids by Pseudomonas sp. 42A2. Biochim Biophys Acta. 1997 Jul 12;1347(1):75-81. doi: 10.1016/s0005-2760(97)00056-8. PMID: 9233689.