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Merck

41707

Sigma-Aldrich

2-C-Methyl-D-erythritol

≥90% (GC)

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C5H12O4
Número de CAS:
Peso molecular:
136.15
Beilstein/REAXYS Number:
5916602
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
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

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
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

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