Urocanic acid

Names

[ CAS No. ]:
104-98-3

[ Name ]:
Urocanic acid

[Synonym ]:
(2E)-3-(1H-Imidazol-4-yl)acrylic acid
urocanoic acid
(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
(E)-3-(1H-imidazol-4-yl)acrylic acid
RARECHEM AL BK 0762
(Z/E)-3-(1H-imidazol-4-yl)-2-propenoic acid
3-(1H-imidazol-4-yl)prop-2-enoic acid
imidazoleacrylicacid
(E)-3-(1H-imidazol-4-yl)-2-propenoic acid
3-imidazol-4-ylacrylic
Urocanate
4-Imidazoleacrylic Acid
2-Propenoic acid, 3-(1H-imidazol-4-yl)-, (2E)-
UROCANINIC ACID
Trans-Urocanic acid
(E)-3-(1H-Imidazol-5-yl)-2-propenoic acid
3-(1H-Imidazol-4-yl)acrylic acid
Urocanic caid
Urocanic acid
3-imidazol-4-yl-acrylic acid
2-propenoic acid, 3-(1H-imidazol-5-yl)-, (2E)-
urosanic acid
4-imidazoleacrylate
MFCD00005203
(2E)-3-(1H-Imidazol-5-yl)acrylic acid
EINECS 203-258-4

Biological Activity

[Description]:

Urocanic acid, produced in the upper layers of mammalian skin, is a major absorber of ultraviolet radiation (UVR).

[Related Catalog]:

Natural Products >> Acids and Aldehydes

Research Areas >> Others

[Target]

Human Endogenous Metabolite

[In Vitro]

Urocanic acid (UCA) is formed in the upper layers of the epidermis where filaggrin, a histidine-rich filamentous protein produced after caspase-14 cleavage of profilaggrin, is broken down by proteinases into component amino acids[1].

[References]

[1]. Gibbs NK, et al. Recent advances in urocanic acid photochemistry, photobiology and photoimmunology. Photochem Photobiol Sci. 2008 Jun;7(6):655-67.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
456.9±20.0 °C at 760 mmHg

[ Melting Point ]:
226-228 °C(lit.)

[ Molecular Formula ]:
C₆H₆N₂O₂

[ Molecular Weight ]:
138.124

[ Flash Point ]:
230.1±21.8 °C

[ Exact Mass ]:
138.042923

[ PSA ]:
65.98000

[ LogP ]:
0.01

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.674

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
SLIGHTLY SOLUBLE

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI3425200

CHEMICAL NAME :: Imidazole-4-acrylic acid

CAS REGISTRY NUMBER :: 104-98-3

BEILSTEIN REFERENCE NO. :: 0081405

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C6-H6-N2-O2

MOLECULAR WEIGHT :: 138.14

WISWESSER LINE NOTATION :: T5M CNJ D1U1VQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Cells - not otherwise specified

DOSE/DURATION :: 1 mmol/L

REFERENCE :: JIDEAE Journal of Investigative Dermatology. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1938- Volume(issue)/page/year: 65,400,1975

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NI3425200

[ HS Code ]:
29332990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 29332990

Articles

Investigation of a Degradant in a Biologics Formulation Buffer Containing L-Histidine.

Pharm. Res. 32 , 2625-35, (2015)

An unknown UV 280 nm absorbing peak was observed by SEC for protein stability samples formulated in L-histidine during a stress stability study. Understanding the source would enhance the confidence i...

Chemical genetics reveals a complex functional ground state of neural stem cells.

Nat. Chem. Biol. 3(5) , 268-273, (2007)

The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain canc...

Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.

Eur. J. Med. Chem. 46 , 1483-98, (2011)

A new series of potential GABA uptake inhibitors starting from of 1H-imidazol-4-ylacetic acid with the carboxylic acid side chain originating from different positions and varying in length have been s...