(±)18-HEPE - ≥97%, ~100 µg/mL in ethanol , CAS No.141110-17-0

CAS: 141110-17-0 Cat. No.: H351199 Formula: C₂₀H₃₀O₃ Molecular Weight: 318.45

GRADE & PURITY ≥97%, ~100 µg/mL in ethanol

Synonyms

18-Hydroxy-5(Z),8(Z),11(Z),14(Z),16(E)-eicosapentaenoic acid | (±)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

(±)18-HEPE is produced by non-enzymatic oxidation of eicosapentaenoic acid. 18-HEPE levels are increased in the plasma and heart, as well as in the supernatant of cultured peritoneal macrophages isolated from fat-1 transgenic mice that are capable of endogenously producing ω-3 fatty acids from ω-6 fatty acids. It reduces increases in cardiac fibrosis and the expression of Nppa, Col1a1, Tgfb1, Cx3cl1, and Adgre1 induced by transverse aortic constriction in a mouse model of cardiac hypertrophy when administered at doses of 1 and 5 µg.

Specifications

Synonyms

18-Hydroxy-5(Z),8(Z),11(Z),14(Z),16(E)-eicosapentaenoic acid | (±)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid

Specifications & Purity

≥97%, ~100 µg/mL in ethanol

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

Canonical Smiles

CCC(C=CC=CCC=CCC=CCC=CCCCC(=O)O)O

IUPAC Name

(5Z,8Z,11Z,14Z,16E)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid

InChIKey

LRWYBGFSVUBWMO-UXNZXXPISA-N

INCHI

1S/C20H30O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,15,17,19,21H,2-3,8-9,14,16,18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-,17-15+

Isomeric SMILES

CCC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O

Molecular Weight

318.45

Reaxy-Rn

29757820

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=29757820&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Eicosanoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Eicosanoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroxyeicosapentaenoic acids
• Alternative Parents: Long-chain fatty acids Hydroxy fatty acids Unsaturated fatty acids Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Hydroxyeicosapentaenoic acid - Long-chain fatty acid - Hydroxy fatty acid - Fatty acid - Unsaturated fatty acid - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Carbonyl group - Organooxygen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.
• External Descriptors: Hydroxy/hydroperoxyeicosapentaenoic acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in DMSO (~50 mg/ml), DMF (~50 mg/ml), PBS (pH 7.2) (~1 mg/ml), and ethanol.
• Refractive Index: n20D1.53 (Predicted)
• Boil Point(°C): 78° C
• Molecular Weight: 318.400 g/mol
• XLogP3: 4.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 318.219 Da
• Monoisotopic Mass: 318.219 Da
• Topological Polar Surface Area: 57.500 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 428.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 5
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 5
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 141110-17-0, the molecular formula is C20H30O3, and the molecular weight is 318.45 g/mol. InChIKey LRWYBGFSVUBWMO-UXNZXXPISA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.