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9-Nitrooleic acid

HCID 11645581
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
875685-44-2
Standard SMILES
CCCCCCCC/C=C(\CCCCCCCC(=O)O)[N+](=O)[O-]
InChIKey
CQOAKBVRRVHWKV-SAPNQHFASA-N
Molecular formula
C18H33NO4
Average molar mass
327.5 g/mol
Monoisotopic mass
327.24095853

Overview

(9E)-9-nitrooctadecenoic acid is a nitro fatty acid that is (9E)-octadec-9-enoic (elaidic) acid substituted by a nitro group at position 9. It has a role as a human metabolite. It is a long-chain fatty acid, a monounsaturated fatty acid and a nitro fatty acid. It is functionally related to an elaidic acid.

Names & identifiers

Preferred name
9-Nitrooleic acid
IUPAC
(E)-9-nitrooctadec-9-enoic acid
English name
9-Nitrooleate
Molecular formula
C18H33NO4
Molecular weight
327.45892

Names & synonyms

875685-44-29-Nitrooleic acidDTXSID301316471RefChem:1075022DTXCID8017463189-nitro-9E-octadecenoic acid(E)-9-nitrooctadec-9-enoic Acid9-Nitro Oleic Acid9-Nitrooleatenitrooleic acidNitroleic Acid(9E)-9-nitrooctadec-9-enoic acid
Show more names
(9E)-9-Nitro-9-octadecenoic Acid9-Octadecenoic acid, 9-nitro-, (9E)-
CHEMBL550762(9E)-9-nitrooctadecenoic acid(9E)-Nitro Oleic Acid9NOA9-nitro-9E-Octadecenoate(9E)-9-Nitrooctadecenoate(e)-9-Nitrooctadec-9-enoateGTPL6296

Database identifiers

CAS
875685-44-2
PubChem CID
11645581
DTXSID
DTXSID301316471
ChEMBL
CHEMBL550762
ChEBI
CHEBI:86329
Nikkaji
J2.361.801J

Properties

Computed structural properties

XLogP
6.7
Topological polar surface area
83.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
15
Heavy atoms
23
Formal charge
0
Complexity
347

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Nitro fatty acids [FA0112]

Physicochemical properties

storage temp.
-20 °C · Store at -20°C
solubility
1 mg/ml · Ethanol: 1 mg/ml
Symbol(GHS)
2 · GHS02
Signal word
Danger
Hazard statements
225 · H225
Precautionary statements
210 · P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

Signal word
Danger
Symbol(GHS)
GHS02
Hazard statements
H225
Precautionary statements
P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

Chemistry & industry

Applications · 3 items

DescriptionNitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleate (LNO2; ), cholesteryl nitrolinoleate, and nitrohydroxylinoleate, represent a new class of endogenous lipid-derived signalling molecules. LNO2 isomers serve as potent endogenous ligands for PPARγ and can also decompose or be metabolized to release nitric oxide. 9-Nitrooleate is one of two regioisomers of nitrooleate, the other being 10-nitrooleate (OA-NO2; used for the mixture of isomers), which are formed by nitration of oleic acid in approximately equal proportions in vivo. Peroxynitrite, acidified nitrite, and myeloperoxidase in the presence of H2O2 and nitrite, all mediate the nitration of oleic acid. OA-NO2 is found in human plasma as the free acid and esterified in phospholipids at concentrations of 619 ± 52 nM and 302 ± 369 nM, respectively. OA-NO2 activates PPARγ approximately 7-fold at a concentration of 1 μM and effectively promotes the differentiation of 3T3-L1 preadiopcytes to adipocytes at 3 μM.

Uses9-Nitrooleic Acid is a bioactive, nitric-oxide derived fatty acid. 9-Nitrooleic Acid II-induced hypertension. 9-Nitrooleic Acid is an endogenous PPAR agonist which may offer an effective and safe therapeutic intervention for obesity and obesity-related conditions.

Uses9-Nitrooleic Acid is a bioactive, nitric-oxide derived fatty acid. 9-Nitrooleic Acid thats acts as an irreversible inhibitor of xanthine oxidoreductase. 9-Nitrooleic Acid is a novel antagonist of Ang II-induced hypertension. 9-Nitrooleic Acid is an endogenous PPAR agonist which may offer an effective and safe therapeutic intervention for obesity and obesity-related conditions.

Suppliers19 total

咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]

Related reactions

1 records
New reaction record
HRID 2360196 reaction equation
HRID 2360196As reactantuspto-grants-2014_04

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
BOC Sciences16314854226 · [email protected]
武汉沃格达生物科技有限公司15071299552 · [email protected]
上海芮晖化工科技有限公司021-31433387 15618786686 · [email protected]
上海宏叶生物科技有限公司400-9205774 400-920-5774 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
河南阿尔法化工有限公司0371-55055611 18137792234 · [email protected]
安徽今昱生物化工产品技术研发有限公司055167162561 13295518198 · [email protected]
上海传芊化工科技中心15869524721 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
BOC Sciences+1-631-485-4226 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
武汉艾美捷科技有限公司4006800868;027-59626688 18771149750 · [email protected]
Additional notes · 1 item

DefinitionChEBI: (9E)-9-nitrooctadecenoic acid is a nitro fatty acid that is (9E)-octadec-9-enoic (elaidic) acid substituted by a nitro group at position 9. It has a role as a human metabolite. It is a long-chain fatty acid, a monounsaturated fatty acid and a nitro fatty acid. It is functionally related to an elaidic acid.