WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 412684
CAS#: 29623-28-7 (free base)
Description: 13(S)HODE is produced by incubation of linoleic acid with plant and mammalian lipoxygenases. It has been shown to inhibit the adhesion of tumor cells to the endothelium at concentrations around 1 µM,1,2 and down regulates the expression of the IRGpIIb/IIIa receptor.
MedKoo Cat#: 412684
Name: 13(S)HODE
CAS#: 29623-28-7 (free base)
Chemical Formula: C18H32O3
Exact Mass: 296.2351
Molecular Weight: 296.45
Elemental Analysis: C, 72.93; H, 10.88; O, 16.19
Related CAS #: 29623-28-7 (free base) 198123-90-9 (ethanolamide)
Synonym: 13(S)HODE; 13S-Hydroxy-9Z,11E-octadecadienoic acid
IUPAC/Chemical Name: (S,9Z,11E)-13-hydroxyoctadeca-9,11-dienoic acid
InChi Key: HNICUWMFWZBIFP-IRQZEAMPSA-N
InChi Code: InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1
SMILES Code: CCCCC[C@H](O)/C=C/C=C\CCCCCCCC(O)=O
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 296.45 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: Fang X, Kaduce TL, Spector AA. 13-(S)-hydroxyoctadecadienoic acid (13-HODE) incorporation and conversion to novel products by endothelial cells. J Lipid Res. 1999 Apr;40(4):699-707. PMID: 10191294.
2: Dong J, Shichiri M, Chung CI, Shibata T, Uchida K, Hagihara Y, Yoshida Y, Ueda H. An open sandwich immunoassay for detection of 13(R,S)-hydroxy-9(E),11(E)-octadecadienoic acid. Analyst. 2017 Feb 27;142(5):787-793. doi: 10.1039/c6an02437h. PMID: 28144646.
3: Li MY, Yuan HL, Ko FW, Wu B, Long X, Du J, Wu J, Ng CS, Wan IY, Mok TS, Hui DS, Underwood MJ, Chen GG. Antineoplastic effects of 15(S)-hydroxyeicosatetraenoic acid and 13-S-hydroxyoctadecadienoic acid in non- small cell lung cancer. Cancer. 2015 Sep 1;121 Suppl 17:3130-45. doi: 10.1002/cncr.29547. PMID: 26331820.
4: Yuan H, Li MY, Ma LT, Hsin MK, Mok TS, Underwood MJ, Chen GG. 15-Lipoxygenases and its metabolites 15(S)-HETE and 13(S)-HODE in the development of non-small cell lung cancer. Thorax. 2010 Apr;65(4):321-6. doi: 10.1136/thx.2009.122747. PMID: 20388757.
5: Spindler SA, Sarkar FH, Sakr WA, Blackburn ML, Bull AW, LaGattuta M, Reddy RG. Production of 13-hydroxyoctadecadienoic acid (13-HODE) by prostate tumors and cell lines. Biochem Biophys Res Commun. 1997 Oct 29;239(3):775-81. doi: 10.1006/bbrc.1997.7471. PMID: 9367845.
6: Mani I, Iversen L, Ziboh VA. Upregulation of nuclear PKC and MAP-kinase during hyperproliferation of guinea pig epidermis: modulation by 13-(S)-hydroxyoctadecadienoic acid (13-HODE). Cell Signal. 1998 Feb;10(2):143-9. doi: 10.1016/s0898-6568(97)00099-5. PMID: 9481490.
7: Tavakoli Yaraki M, Karami Tehrani F. Apoptosis Induced by 13-S-hydroxyoctadecadienoic acid in the Breast Cancer Cell Lines, MCF-7 and MDA- MB-231. Iran J Basic Med Sci. 2013 Apr;16(4):661-9. PMID: 24250949; PMCID: PMC3830757.
8: Tavakoli Yaraki M, Karami Tehrani F. Apoptosis Induced by 13-S-hydroxyoctadecadienoic acid in the Breast Cancer Cell Lines, MCF-7 and MDA- MB-231. Iran J Basic Med Sci. 2013 Apr;16(4):653-9. PMID: 24250946; PMCID: PMC3821886.
9: Shureiqi I, Wojno KJ, Poore JA, Reddy RG, Moussalli MJ, Spindler SA, Greenson JK, Normolle D, Hasan AA, Lawrence TS, Brenner DE. Decreased 13-S-hydroxyoctadecadienoic acid levels and 15-lipoxygenase-1 expression in human colon cancers. Carcinogenesis. 1999 Oct;20(10):1985-95. doi: 10.1093/carcin/20.10.1985. PMID: 10506115.
10: Liu B, Khan WA, Hannun YA, Timar J, Taylor JD, Lundy S, Butovich I, Honn KV. 12(S)-hydroxyeicosatetraenoic acid and 13(S)-hydroxyoctadecadienoic acid regulation of protein kinase C-alpha in melanoma cells: role of receptor- mediated hydrolysis of inositol phospholipids. Proc Natl Acad Sci U S A. 1995 Sep 26;92(20):9323-7. doi: 10.1073/pnas.92.20.9323. Erratum in: Proc Natl Acad Sci U S A 1995 Nov 21;92(24):11322. PMID: 7568126; PMCID: PMC40977.
