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41707

Sigma-Aldrich

2-C-Methyl-D-erythritol

≥90% (GC)

Synonym(s):

(2S,3R)-2-Methyl-1,2,3,4-tetrahydroxybutane, (2S,3R)-2-Methylbutane-1,2,3,4-tetrol

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About This Item

Empirical Formula (Hill Notation):
C5H12O4
CAS Number:
58698-37-6
Molecular Weight:
136.15
Beilstein:
5916602
MDL number:
MFCD17215928
UNSPSC Code:
12352201
PubChem Substance ID:
329756141
NACRES:
NA.25

biological source

(Carum ajowan fruit)

Quality Level

100

Assay

≥90% (GC)

form

viscous liquid (clear)

color

colorless

storage temp.

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

InChI key

HGVJFBSSLICXEM-UHNVWZDZSA-N

Related Categories

General description

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

Biochem/physiol Actions

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.

Other Notes

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
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
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)
T Ishikawa et al.
Chemical & pharmaceutical bulletin, 49(7), 840-844 (2001-07-18)
From the water-soluble portion of the methanol extract of the fruit of Carum ajowan (ajowan), which has been used as a spice and medicine, 25 compounds, including five new monoterpenoid glucosides, a new monoterpenoid, two new aromatic compound glucosides, and
Biosynthesis of 2-C-methyl-D-erythritol, a putative C5 intermediate in the mevalonate independent pathway for isoprenoid biosynthesis.
Duvold, T., et al.
Tetrahedron Letters, 38, 4769-4772 (1997)
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