2-Oxoadipic acid (HCID 71)

Overview

2-oxoadipic acid is an oxo dicarboxylic acid that is adipic acid substituted by an oxo group at position 2. It has a role as a mouse metabolite and a human urinary metabolite. It is functionally related to an adipic acid. It is a conjugate acid of a 2-oxoadipate(2-).

Names & identifiers

Preferred name: 2-Oxoadipic acid
IUPAC: 2-oxohexanedioic acid
English name: 2-Oxoadipic acid, 98
Molecular formula: C6H8O5
Molecular weight: 160.12

Names & synonyms

2-Oxoadipic acid2-Oxohexanedioic acid3184-35-8Oxoadipic acidalpha-Ketoadipic acid2-oxoadipate2-Ketoadipic acidHexanedioic acid, 2-oxo-2-ketoadipatealpha-Oxoadipic acidalpha-ketoadipate2-keto-adipate

Show more names

2-oxoadipicaciA-KETOADIPIC ACIDalpha-ketoadipicacid2-Oxoadipic acid, 98

2-oxohexanedionic acidBB72FKL1M2DTXSID20185702CHEBI:15753RefChem:857770DTXCID201081932-Oxo-hexanedioic acidOxoadipate

Database identifiers

CAS: 3184-35-8
PubChem CID: 71
DTXSID: DTXSID20185702
ChEBI: CHEBI:15753
UNII: BB72FKL1M2
EC Number: 636-531-5
Nikkaji: J39.063A

Properties

Computed structural properties

XLogP: -0.5
Topological polar surface area: 91.7 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 5
Heavy atoms: 11
Formal charge: 0
Complexity: 183

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]

Melting Point127 °C

Physical DescriptionSolid

Collision Cross Section · 3 items

132.2 Å² [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

129.65 Å² [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

132.6 Å² [M-2H+Na]-

Physicochemical properties

Melting point: 123 · 123-125 °C(lit.)
Boiling point: 364.3 · 364.3±25.0 °C(Predicted)
Density: 1.405 · 1.405±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: 250 mg/ml, · Water: 250 mg/ml, sonicated
form: A solid
pka: 2.53 · 2.53±0.54(Predicted)
color: Off-white to light yellow
InChI: 1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)
InChIKey: FGSBNBBHOZHUBO-UHFFFAOYSA-N
SMILES: OC(=O)CCCC(=O)C(O)=O
LogP: -1.22 · -1.220 (est)
FDA UNII: 72 FKL1M2 · BB72FKL1M2
UNSPSC Code: 12352106 · 12352106
NACRES: 25 · NA.25
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319
Precautionary statements: 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 1 · 1
HS Code: 29183000 · 29183000
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationHexanedioic acid, 2-oxo-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxicology

Health EffectsChronically high levels of oxoadipic acid are associated with at least 2 inborn errors of metabolism including: 2-aminoadipic and 2-oxoadipic aciduria.

Toxicity SummaryIn the matrix of mitochondria, 2-oxoadipate is decarboxylated to glutaryl-CoA by the 2-oxoadipate dehydrogenase complex and then converted to acetyl-CoA. Accumulation of oxoadipic acid in the body has been shown to be toxic.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 1
hs_code: 29183000
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2
Precautionary statements: P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313

Chemistry & industry

Pharmacology

Cellular LocationsMitochondria

Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria

Uses & manufacturing

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Applications

UsesOxoadipic acid is a key metabolite of the essential amino acids tryptophan and lysine.

Upstream & downstream products

Downstream products

DL-2-Aminoadipic acid

Suppliers50 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]

陕西科贝莱药物研发有限公司13119135307 · [email protected]

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]

陕西格列弗生物科技研究有限责任公司13892423764 · [email protected]

湖北万得化工有限公司15377098680 15377098680 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 2-oxoadipic acid is an oxo dicarboxylic acid that is adipic acid substituted by an oxo group at position 2. It has a role as a mouse metabolite and a human urinary metabolite. It is functionally related to an adipic acid. It is a conjugate acid of a 2-oxoadipate(2-).