15-hydroxyicosatetraenoic acid

15-Hydroxyeicosatetraenoic acid

Names
IUPAC name (5Z,8Z,11Z,13E,15S)-15-Hydroxyicosa-5,8,11,13-tetraenoic acid
Other names 15-HETE, 15(S)-HETE, 15(S)-HETE
Identifiers
CAS Number	54845-95-3
3D model (Jmol)	Interactive image
ChemSpider	4444307
ECHA InfoCard	100.214.805
IUPHAR/BPS	3401
PubChem	5280724
InChI InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1 Key: JSFATNQSLKRBCI-VAEKSGALSA-N
SMILES CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
Properties
Chemical formula	C20H32O3
Molar mass	320.47 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

15-Hydroxyeicosatetraenoic acid (also termed 15-HETE, 15(S)-HETE, and 15S-HETE) is an endogenous eicosanoid, i.e. a metabolite of arachidonic acid. Various cell types and tissues first produce 15-Hydroperoxyicosatetraenoic acid (15-HpETE). These initial hydroperoxy products are extremely short lived in cells: if not otherwise metabolized, they are reduced to 15-HETE. Both these molecules are hormone-like and paracrine signalling agents, involved in inflammation response, but often are further metabolized to a wide range of products that are much more potent, including eoxins.

The production and actions of these molecules and their metabolites often differ greatly depending on cell-type or tissue-type studied. In many ways they are analogous to the more abundant 5-HETE and 5-HPETE.

15-HETE (15(S)-HETE, or 15S-HETE) is unambiguously designated by a shortened version of its IUPAC name, (15S)-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid, where S refers to the absolute configuration of the point chirality of the hydroxyl functional group at carbon position 15. Its enantiomer is (15R)-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid, i.e. 15(R)-HETE or 15R-HETE. The substance also has Z- and E-stereoisomers (an example of cis–trans isomerism) about each of its double bond moieties at carbon positions 5, 8, 11, and 13.

These stereoisomers are produced from corresponding stereoisomers of 15-HpETE, namely (15S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (15(S)-HpETE), (15R)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (15(R)-HpETE), and/or a racemic mixture of both stereoisomers. These initial hydroperoxy products are extremely short lived in cells: if not otherwise metabolized, they are reduced to their 15(S)-HETE or 15(R)-HETE analogs.