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4,6-DIOXOHEPTANOIC ACID

4,6-DIOXOHEPTANOIC ACID structure

CAS No:
51568-18-4
Formula:
C7H10O4
Chemical Name:
4,6-DIOXOHEPTANOIC ACID
Synonyms:
4,6-DIOXOHEPTANOIC ACID;Succinylacetone-3,4,5,6,7-13C5;4,6-Dioxoheptanoic acid-3,4,5,6,7-13C5;[13C7]-Succinylacetone;Heptanoic acid, 4,6-dioxo-;4,6-dioxoheptanoicaci;4,6-Dioxoheptanoic acid (mixture of isomers);Succinylacetone in Water
Categories:
Analytical Chemistry > Food Safety

Description

4,6-Dioxoheptanoic acid is a potent inhibitor of heme biosynthesis.

Solid

4,6-dioxoheptanoic acid is a dioxo monocarboxylic acid that is heptanoic acid in which oxo groups replace the hydrogens at positions 4 and 6. It is an abnormal metabolite of the tyrosine metabolic pathway and a marker for type 1 tyrosinaemia. It has a role as a human metabolite. It is a beta-diketone and a dioxo monocarboxylic acid.

Succinylacetone (4,6-dioxoheptanoic acid), is a result of tyrosine metabolism disorder. The synthesis of this medium-chain keto acid in the body is due to the reduced activity of the enzyme fumarylacetoacetate hydrolase. Succinylacetone is an acidogen, its high concentrations can lead to metabolic acidosis, which leads to damage to the liver, kidneys, heart, and nervous system. Succinylacetone appears to be an oncometabolite because patients with high levels of this compound often develop hepatocellular carcinoma.Succinylacetone is widely used in research as an inhibitor of the enzyme 5-aminolevulinic acid dehydratase (ALAD), which plays a key role in heme biosynthesis.The product is used primarily as a control for MS/MS.

White Solid

4,6-DIOXOHEPTANOIC ACID Basic Attributes

Molecular Weight：

158.15

Exact Mass：

158.15

UNII：

KZ0KV2Q190

NSC Number：

174804

DSSTox ID：

DTXSID50199519

Color/Form：

White to Off-White

HScode：

2918300090

Characteristics

PSA：

71.4

XLogP3：

-0.8

Appearance：

powder

Density：

1.189±0.06 g/cm3(Predicted)

Melting Point：

66-67 °C(lit.)

Boiling Point：

318.7±17.0 °C(Predicted)

Flash Point：

160.8ºC

Refractive Index：

1.455

Water Solubility：

2.579e+005 mg/L @ 25 °C (est)

Storage Conditions：

2-8°C

PKA：

4.54±0.17(Predicted)

Collision Cross Section：

131.44 Å² [M-H]- [CCS Type: DT, Method: stepped-field]

Critical Temperature & Pressure：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

26-36

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

36/37/38

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

MeSH Entry Terms：

4,6-dioxoheptanoic acid

4,6-DIOXOHEPTANOIC ACID Use and Manufacturing

Succinylacetone (SA) is a specific marker for the inherited metabolic disease, hepatorenal tyrosinemia. It was developed a stable-isotopequid urine using a 13C4-SA as internal standard.

4,6-Dioxoheptanoic acid has been used:as component of dendritic cell conditioning medium and in the inhibition of ALA dehydratase (ALAD) in dendritic cells(50)as an inhibitor of heme biosynthesis in human mononuclear cells(51) and HeLa cells(52)as a standard for the quantification of succinylacetone from Plasmodium falciparum cultures(53)

Computed Properties

Molecular Weight:158.15
XLogP3:-0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:158.05790880
Monoisotopic Mass:158.05790880
Topological Polar Surface Area:71.4
Heavy Atom Count:11
Complexity:183
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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4,6-Dioxoheptanoic acid

CAS No.: 51568-18-4

Content: 99.00%

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