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41707

Sigma-Aldrich

2-C-Methyl-D-erythritol

≥90% (GC)

Synonym(e):

(2S,3R)-2-Methyl-1,2,3,4-tetrahydroxybutan, (2S,3R)-2-Methylbutan-1,2,3,4-tetrol

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About This Item

Empirische Formel (Hill-System):
C5H12O4
CAS-Nummer:
58698-37-6
Molekulargewicht:
136.15
Beilstein:
5916602
MDL-Nummer:
MFCD17215928
UNSPSC-Code:
12352201
PubChem Substanz-ID:
329756141
NACRES:
NA.25

Biologische Quelle

(Carum ajowan fruit)

Qualitätsniveau

100

Assay

≥90% (GC)

Form

viscous liquid (clear)

Farbe

colorless

Lagertemp.

2-8°C

SMILES String

C[C@](O)(CO)[C@H](O)CO

InChI

1S/C5H12O4/c1-5(9,3-7)4(8)2-6/h4,6-9H,2-3H2,1H3/t4-,5+/m1/s1

InChIKey

HGVJFBSSLICXEM-UHNVWZDZSA-N

Verwandte Kategorien

Allgemeine Beschreibung

(2S,3R)-2-methylbutane-1,2,3,4-tetrol was identified as a glucide in methanol extracts of Carum ajowan fruit.

Biochem./physiol. Wirkung

Metabolite of the non-mevalonate MEP pathway, generally found in prokaryotes, as precursor to isoprenoids as well as non-isoprenoids like vitamins. As this pathway is not present in humans, it is of interest for the development of bacterium-specific drugs in the search for treatments of infectious diseases.

Sonstige Hinweise

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Incorporation of 2-C-methyl-D-erythritol, a putative isoprenoid precursor in the mevalonate-independent pathway, into ubiquinone and menaquinone of Escherichia coli.
Duvold, T., et al.
Tetrahedron Letters, 38, 6181-6184 (1997)
Jin-Zheng Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(1), 355-361 (2019-12-28)
The methylerythritol phosphate (MEP) pathway is responsible for producing isoprenoids, metabolites with essential functions in the bacterial kingdom and plastid-bearing organisms including plants and Apicomplexa. Additionally, the MEP-pathway intermediate methylerythritol cyclodiphosphate (MEcPP) serves as a plastid-to-nucleus retrograde signal. A suppressor
Gur Pines et al.
Molecules (Basel, Switzerland), 25(9) (2020-05-15)
Drug resistance is a major healthcare challenge, resulting in a continuous need to develop new inhibitors. The development of these inhibitors requires an understanding of the mechanisms of resistance for a critical mass of occurrences. Recent genome editing technologies based
Hiroyuki Enomoto et al.
Journal of plant physiology, 161(8), 977-980 (2004-09-24)
2-C-methyl-D-erythritol, a soluble carbohydrate that is not ubiquitously found in higher plants, was detected in the ethanol extract from Phlox subulata petals and isolated using HPLC. The isolated compound was identified by 1H-NMR, 13C-NMR and Cl-MS spectra. 2-C-methyl-D-erythritol was a
Rong Guo et al.
Bioscience, biotechnology, and biochemistry, 82(11), 1902-1910 (2018-08-22)
RT-qPCR has been widely used for gene expression analysis in recent years. The accuracy of this technique largely depends on the selection of suitable reference genes. In order to facilitate gene expression analysis in wild and cultivated Cannabis, the expression
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