9(S)-HODE Chemical Properties

Boiling point:

416.1±33.0 °C(Predicted)

Density 

0.970±0.06 g/cm3(Predicted)

Flash point:

14℃

storage temp. 

-20°C

solubility 

DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 50 mg/ml; PBS pH 7.2: 1 mg/ml

form 

ethanol solution (1 mg/mL)

pka

4.78±0.10(Predicted)

color 

colorless to light yellow

InChI

1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/t17-/m1/s1

InChIKey

NPDSHTNEKLQQIJ-UINYOVNOSA-N

SMILES

CCCCC/C=C\C=C\[C@@H](O)CCCCCCCC(O)=O

Safety Information

Hazard Codes 

F

Risk Statements 

11

Safety Statements 

7-16

RIDADR 

UN1170 - class 3 - PG 2 - Ethanol, solution

WGK Germany 

1

Storage Class

3 - Flammable liquids

Hazard Classifications

Eye Irrit. 2
Flam. Liq. 2

9(S)-HODE Usage And Synthesis

Description

9(S)-HODE is produced by the lipoxygenation of linoleic acid in both plants and animals. It has been detected in atherosclerotic plaques, as an esterified component of membrane phospholipids and in oxidized LDL particles.

Uses

9S-HODE (Alpha-dimorphecolic acid) is an octadecadienoic acid and the main active derivative of linoleic acid, which can reduce the viability of HL-60 cells and induce apoptosis. 9S-HODE is rich in lipid peroxidation (LPO) products and is almost an ideal marker for LPO[1][2].

Definition

ChEBI: A 9-HODE in which the 9-hydroxy group has S-stereochemistry.

IC 50

Human Endogenous Metabolite

References

[1] Liu S, et al. Linoleic acid derivatives target miR-361-3p/BTG2 to confer anticancer effects in acute myeloid leukemia. J Biochem Mol Toxicol. 2023 Nov;37(11):e23481. DOI:10.1002/jbt.23481
[2] Spiteller P, et al. 9-Hydroxy-10, 12-octadecadienoic acid (9-HODE) and 13-hydroxy-9, 11-octadecadienoic acid (13-HODE): excellent markers for lipid peroxidation[J]. Chemistry and Physics of Lipids, 1997, 89(2): 131-139.

9(S)-HODE(73543-67-6)Related Product Information

• Undecenoic acid
• 9(S)-HPODE
• CIS-10,TRANS-12-CONJUGATEDLINOLEICACID
• 13(S)-HODE CHOLESTERYL ESTER
• 13(R)-HODE CHOLESTERYL ESTER
• (+/-)13-HODE CHOLESTERYL ESTER
• 9(R)-HODE CHOLESTERYL ESTER
• HODE,(+/-)13-HODE
• 13(S)-HODE-D4
• 9(S)-HODE
• (+/-)9-HODE
• 9(S)-HODE-D4
• 13(R)-HODE
• 9(S)-HODE CHOLESTERYL ESTER
• 13(S)-HODE-BIOTIN
• (+/-)9-HODE CHOLESTERYL ESTER
• Hydroxyoctadecadienoic Acid 13(S) (HODE)
• 9(R)-HODE