ChemicalBook > CAS DataBase List > (+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID

(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID

Product Name
(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID
CAS No.
88852-33-9
Chemical Name
(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID
Synonyms
(+/-)15-HEPE;WLKCSMCLEKGITB-XWJJKCKWSA-N;15-hydroxy-eicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid;(+/-)-15-Hydroxy-5Z,8Z,11Z,13E,17Z-eicosadienoic acid;(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID;(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID;5,8,11,13,17-Eicosapentaenoic acid, 15-hydroxy-, (5Z,8Z,11Z,13E,17Z)-
CBNumber
CB4160353
Molecular Formula
C20H30O3
Formula Weight
318.45
MOL File
88852-33-9.mol
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(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID Property

Boiling point:
488.0±45.0 °C(Predicted)
Density 
0.997±0.06 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
0.1 M Na2CO3: 2 mg/ml; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS pH 7.2: 0.8 mg/ml
pka
4.75±0.10(Predicted)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
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N-Bromosuccinimide Price

Cayman Chemical
Product number
32700
Product name
(±)15-HEPE
Purity
≥98%
Packaging
25μg
Price
$95
Updated
2024/03/01
Cayman Chemical
Product number
32700
Product name
(±)15-HEPE
Purity
≥98%
Packaging
50μg
Price
$181
Updated
2024/03/01
Cayman Chemical
Product number
32700
Product name
(±)15-HEPE
Purity
≥98%
Packaging
100μg
Price
$342
Updated
2024/03/01
AHH
Product number
MT-15004
Product name
(+/-)-15-Hydroxy-5Z,8Z,11Z,13E,17Z-eicosadienoic acid
Purity
98%
Packaging
0.001g
Price
$645
Updated
2021/12/16
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(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID Chemical Properties,Usage,Production

Description

(±)15-HEPE is a racemic mixture of the monohydroxy fatty acids 15(R)-HEPE and 15(S)-HEPE . 15(S)-HEPE is formed from EPA via a 15(S)-HpEPE intermediate, which is produced by 15-lipoxygenase (15-LO) and reduced by glutathione peroxidase (GPX).1,2 (±)15-HEPE is active against P. acnes and S. aureus (MICs = 128 and 512 mg/L, respectively).3 It inhibits aggregation of isolated rat neutrophils induced by the formyl peptide receptor agonist fMLP (IC50 = 4.7 μM).4 Bronchoalveolar lavage fluid (BALF) levels of (±)15-HEPE are increased in patients with allergic asthma or COVID-19.5,6

Definition

ChEBI: 15-HEPE is a hydroxyicosapentaenoic acid that consists of 5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid bearing an additional 15-hydroxy substituent. It has a role as a mouse metabolite. It is a HEPE and a hydroxy polyunsaturated fatty acid.

References

1. Miller, C., Yamaguchi, R.Y., and Ziboh, V.A. Guinea pig epidermis generates putative anti-inflammatory metabolites from fish oil polyunsaturated fatty acids Lipids 24(12),998-1003(1989).
2. Tan, L., Xin, X., Zhai, L., et al. Drosophila fed ARA and EPA yields eicosanoids, 15S-hydroxy-5Z,8Z, 11Z, 13E-eicosatetraenoic acid, and 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid Lipids 51(4),435-449(2016).
3. Desbois, A.P., and Lawlor, K.C. Antibacterial activity of long-chain polyunsaturated fatty acids against Propionibacterium acnes and Staphylococcus aureus Mar. Drugs 11(11),4544-4557(2013).
4. Lam, B., Marcinkiewicz, E., and Wong, P.Y.-K. Transformation of 15-hydroperoxyeicosapentaenoic acid into mono- and dihydroxyeicosapentaenoic acids by human platelets Drugs affecting leukotrienes and other eicosanoid pathways ,167-180(1985).
5. Lundstr?m, S.L., Yang, J., K?llberg, H.J., et al. Allergic asthmatics show divergent lipid mediator profiles from healthy controls both at baseline and following birch pollen provocation PLoS One 7(3),e33780(2012).
6. Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients FASEB J. 35(6),e21666(2021).

(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID Suppliers

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88852-33-9, (+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACIDRelated Search:

15(S)-HPEPE [1-14C] 15(S)-HEPE 15(S)-HPEPE (+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID

  • (+/-)15-HEPE
  • (+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID
  • (+/-)-15-Hydroxy-5Z,8Z,11Z,13E,17Z-eicosadienoic acid
  • WLKCSMCLEKGITB-XWJJKCKWSA-N
  • 15-hydroxy-eicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid
  • (+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID
  • 5,8,11,13,17-Eicosapentaenoic acid, 15-hydroxy-, (5Z,8Z,11Z,13E,17Z)-
  • 88852-33-9