Skip to Content
Merck
All Photos(1)

Documents

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)

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

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)
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
Magda Claeys et al.
Science (New York, N.Y.), 303(5661), 1173-1176 (2004-02-21)
Detailed organic analysis of natural aerosols from the Amazonian rain forest showed considerable quantities of previously unobserved polar organic compounds, which were identified as a mixture of two diastereoisomeric 2-methyltetrols: 2-methylthreitol and 2-methylerythritol. These polyols, which have the isoprene skeleton
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)
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
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