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Uric acid

Uric acid structure

CAS No:
69-93-2
Formula:
C5H4N4O3
Chemical Name:
Uric acid
Synonyms:
1H-Purine-2,6,8(3H)-trione,7,9-dihydro-;Uric acid;7,9-Dihydro-1H-purine-2,6,8(3H)-trione;Lithic acid;Purine-2,6,8(1H,3H,9H)-trione;2,6,8-Trioxypurine;1H-Purine-2,6,8-triol;2,6,8-Trioxopurine;2,6,8-Trihydroxypurine;NSC 3975;Uric acid hyperuricemia;2,3,6,7,8,9-Hexahydro-1H-purine-2,6,8-trione;530-13-2;13154-20-6;33278-42-1;34318-07-5;42911-28-4;42911-27-3;42911-25-1
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

Uric acid is an endogenous antioxidant that scavenges reactive oxygen species (ROS) including singlet oxygen, oxygen radicals, and peroxynitrite.

Solid

7,9-dihydro-1H-purine-2,6,8(3H)-trione is an oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a tautomer of a 2,6-dihydroxy-7,9-dihydro-8H-purin-8-one, a 9H-purine-2,6,8-triol, a 7H-purine-2,6,8-triol, a 1H-purine-2,6,8-triol and a 5,7-dihydro-1H-purine-2,6,8(9H)-trione.|Uric acid is the last product of purine metabolism in humans. The formation of uric acid is through the enzyme xanthine oxidase, which oxidizes oxypurines. Normally a small amount of uric acid is present in the body, but when there is an excess amount in the blood, called hyperuricemia, this can lead to gout and formation of kidney stones. As a therapeutic agent, it is known that uric acid is increased in response to oxidative stress, and as such, uric acid acts as an antioxidant. At present (August 2013), there is no approved formulation or indication for uric acid. In one country, Spain, uric acid is an investigational drug in a phase 3 trial studying its effects as an adjunct to alteplase in acute ischemic stroke.|Uric Acid is a white tasteless odorless crystalline product of protein metabolism, found in the blood and urine, as well as trace amounts found in the various organs of the body. It can build up and form stones or crystals in various disease states.|An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.

Uric acid Basic Attributes

Molecular Weight：

168.11

Exact Mass：

168.11

BRN：

156158

EC Number：

200-720-7

UNII：

268B43MJ25

NSC Number：

3975

DSSTox ID：

DTXSID3042508

NCI Thesaurus Code：

C62652

HScode：

2933990090

Characteristics

PSA：

99.3

XLogP3：

-2.17

Appearance：

White to off-white crystalline

Density：

1.003-1.010 g/cm³

Melting Point：

310 °C (decomp)

Boiling Point：

863ºC at 760 mmHg

Flash Point：

475.7ºC

Refractive Index：

1.721

Water Solubility：

soluble in 1M sodium hydroxide solution. Slightly soluble in water. Insoluble in ether and alcohol.

Storage Conditions：

Store at RT.

PKA：

5.4None

Collision Cross Section：

131 Å² [M+H]+ [CCS Type: DT, Method: stepped-field]|143.5 Å² [M+Na]+ [CCS Type: DT, Method: stepped-field]|127.08 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|130.7 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|125.5 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|126.93 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|126.2 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

33-36/37/38

safety instructions：

24/25-36-26

RTECS Number：

YU7050080

Marks：

Stability/Shelf Life：

Stable. Incompatible with acids, bases, oxidising agents.

GHS Classification：

Not Classified

Drug Information

Drug Indication：

At present (August 2013), there is no approved indication for uric acid. The potential therapeutic use for uric acid is as an adjunct in acute ischemic stroke.

Pharmacology：

Uric acid is a strong reducing agent (donates electrons) and an antioxidant. Normally in humans, one of the main antioxidants in plasma is uric acid. Several animal studies have found that animals given exogenous uric acid within 3 hours after a stroke had decreased infarct volume, improved neurologic function, and diminished inflammatory responses providing evidence for the neuroprotective effects of uric acid. In some early human studies, uric acid has so far shown similar neuroprotective effects, in both the cortex and subcortex areas, due to its antioxidant effects such as decreased lipid peroxidation, and there appears to be no significant toxicities.

MeSH：

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

Absorption：

Uric acid is eliminated by the kidneys.

Metabolism/Metabolites：

In higher primates and humans, the enzyme, uricase, is absent, and thus uric acid is not further metabolized and is excreted. In all other mammals, uric acid is metabolized by uricase to allantoin, which is then excreted.

Mechanism of Action：

The exact mechanism of action for uric acid's antioxidant effects have not yet been elucidated.

MeSH Entry Terms：

2,6,8-Trihydroxypurine

Uric acid Use and Manufacturing

Uses

A xanthine oxidase product.

Manufacturing Info：

1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-: ACTIVE

Use Classification：

Cosmetics -> Buffering; Skin conditioning

Computed Properties

Molecular Weight:168.11
XLogP3:-1.9
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:3
Exact Mass:168.02834000
Monoisotopic Mass:168.02834000
Topological Polar Surface Area:99.3
Heavy Atom Count:12
Complexity:332
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Uric acid

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