Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service