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Sigma-Aldrich

Fumaric acid

≥99.0% (T)

Synonym(s):

(2E)-2-Butenedioic acid, trans-Butenedioic acid

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About This Item

Linear Formula:
HOOCCH=CHCOOH
CAS Number:
110-17-8
Molecular Weight:
116.07
Beilstein/REAXYS Number:
605763
EC Number:
203-743-0
MDL number:
MFCD00002700
UNSPSC Code:
12352100
eCl@ss:
39021709
PubChem Substance ID:
329757345
NACRES:
NA.21

vapor pressure

1.7 mmHg ( 165 °C)

Quality Level

200

grade

purum

assay

≥99.0% (T)

form

powder

autoignition temp.

1364 °F

expl. lim.

40 %

mp

298-300 °C (subl.) (lit.)

solubility

95% ethanol: soluble 0.46 g/10 mL, clear, colorless

SMILES string

OC(=O)\C=C\C(O)=O

InChI

1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

InChI key

VZCYOOQTPOCHFL-OWOJBTEDSA-N

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General description

Fumaric acid can be prepared by fermentation by employing Rhizopus species. Recently, industrial-scale synthesis of fumaric acid from renewable feedstocks and lignocellulosic biomass has been proposed

Application

Fumaric acid has been used as a standard for the quantitative determination of phenolic compounds in nettle samples by HPLC.
Fumaric acid may be used in the preparation of L-Lysine-fumaric acid crystals. It may also be employed for the industrial manufacture of synthetic resins and eco-friendly/biodegradable polymers.

Analysis Note

sublimes at 165°C at 1.7 mm pressure (Lit.)

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

523.4 °F

flash_point_c

273 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD4003
BCCB9913
BCCB7430
BCCB3936
BCCB3232

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Fumaric acid European Pharmacopoeia (EP) Reference Standard

F0600000

Fumaric acid

Transport and metabolism of fumaric acid in Saccharomyces cerevisiae in aerobic glucose-limited chemostat culture.
Shah, Mihir V., et al.
Yeast (2016)
High production of fumaric acid from xylose by newly selected strain Rhizopus arrhizus RH 7-13-9. Bioresource technology
Liu H, et al.
Bioresource Technology, 186, 348-350 (2015)
N Cao et al.
Applied and environmental microbiology, 62(8), 2926-2931 (1996-08-01)
An integrated system of simultaneous fermentation-adsorption for the production and recovery of fumaric acid from glucose by Rhizopus oryzae was investigated. The system was constructed such that growing Rhizopus mycelia were self-immobilized on the plastic discs of a rotary biofilm
Vibrational spectra and second harmonic generation in molecular complexes of L-lysine with L-tartaric, D, L-malic, acetic, arsenous, and fumaric acids.
Marchewka MK, et al.
Crystal Growth & Design, 3(4), 587-592 (2003)
Bas J Meussen et al.
Applied microbiology and biotechnology, 94(4), 875-886 (2012-04-25)
Rhizopus oryzae is a filamentous fungus belonging to the Zygomycetes. It is among others known for its ability to produce the sustainable platform chemicals L: -(+)-lactic acid, fumaric acid, and ethanol. During glycolysis, all fermentable carbon sources are metabolized to
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