fumaric acid

Names

[ CAS No. ]:
110-17-8

[ Name ]:
fumaric acid

[Synonym ]:
U-1149
FEMA 2488
FUMARSAEURE
but-2-en-1,4-dioic acid
TMEDA
trans-2-Butenedioic Acid
Fumarsure
trans-butenedioic acid
Fumaric acid
fumaric
EINECS 203-743-0
MFCD00002700
Boletic acid

Biological Activity

[Description]:

Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

[Related Catalog]:

Natural Products >> Acids and Aldehydes

Research Areas >> Cancer

Research Areas >> Metabolic Disease

[Target]

Human Endogenous Metabolite

[References]

[1]. Whelan DT, et al. Fumaric aciduria: a new organic aciduria, associated with mental retardation and speech impairment. Clin Chim Acta. 1983 Aug 31;132(3):301-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
355.5±25.0 °C at 760 mmHg

[ Melting Point ]:
298-300 °C (subl.)(lit.)

[ Molecular Formula ]:
C₄H₄O₄

[ Molecular Weight ]:
116.072

[ Flash Point ]:
183.0±19.7 °C

[ Exact Mass ]:
116.010956

[ PSA ]:
74.60000

[ LogP ]:
-0.01

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.526

[ Stability ]:
Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible.

[ Water Solubility ]:
0.63 g/100 mL (25 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LS9625000

CHEMICAL NAME :: Fumaric acid

CAS REGISTRY NUMBER :: 110-17-8

BEILSTEIN REFERENCE NO. :: 0605763

LAST UPDATED :: 199710

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C4-H4-O4

MOLECULAR WEIGHT :: 116.08

WISWESSER LINE NOTATION :: QV1U1VQ -T

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9300 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 587 mg/kg

TOXIC EFFECTS :: Gastrointestinal - other changes Liver - other changes Blood - hemorrhage

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6800 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - excitement Lungs, Thorax, or Respiration - respiratory stimulation

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

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

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - excitement Lungs, Thorax, or Respiration - respiratory stimulation

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 5 gm/kg

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

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 40 mg/kg

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 77,750,1986 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 33940 No. of Facilities: 2317 (estimated) No. of Industries: 27 No. of Occupations: 44 No. of Employees: 30637 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 33940 No. of Facilities: 5692 (estimated) No. of Industries: 40 No. of Occupations: 58 No. of Employees: 136448 (estimated) No. of Female Employees: 48919 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36

[ Safety Phrases ]:
S26

[ RIDADR ]:
UN 9126

[ WGK Germany ]:
1

[ RTECS ]:
LS9625000

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2942000000

Articles

A metabolic-based approach to improve xylose utilization for fumaric acid production from acid pretreated wheat bran by Rhizopus oryzae.

Bioresour. Technol. 180 , 119-27, (2015)

In this work, wheat bran (WB) was utilized as feedstock to synthesize fumaric acid by Rhizopus oryzae. Firstly, the pretreatment process of WB by dilute sulfuric acid hydrolysis undertaken at 100°C fo...

Physiology and pathophysiology of organic acids in cerebrospinal fluid.

J. Inherit. Metab. Dis. 16(4) , 648-69, (1993)

Concentrations of organic acids in cerebrospinal fluid (CSF) appear to be directly dependent upon their rate of production in the brain. There is evidence that the net release of short-chain monocarbo...

HMDB: a knowledgebase for the human metabolome.

Nucleic Acids Res. 37(Database issue) , D603-10, (2009)

The Human Metabolome Database (HMDB, http://www.hmdb.ca) is a richly annotated resource that is designed to address the broad needs of biochemists, clinical chemists, physicians, medical geneticists, ...