41707
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:
Molecular Weight:
136.15
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
5916602
Product Name
2-C-Methyl-D-erythritol, ≥90% (GC)
InChI
1S/C5H12O4/c1-5(9,3-7)4(8)2-6/h4,6-9H,2-3H2,1H3/t4-,5+/m1/s1
SMILES string
C[C@](O)(CO)[C@H](O)CO
InChI key
HGVJFBSSLICXEM-UHNVWZDZSA-N
biological source
(Carum ajowan fruit)
assay
≥90% (GC)
form
viscous liquid (clear)
color
colorless
storage temp.
2-8°C
Quality Level
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.
General description
(2S,3R)-2-methylbutane-1,2,3,4-tetrol was identified as a glucide in methanol extracts of Carum ajowan fruit.
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
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
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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