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56845

Sigma-Aldrich

L-(+)-Erythrulose

≥85% (HPLC)

Synonym(s):

S-1,3,4-Trihydroxy-2-butanone, L-Glycero-2-tetrulose

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About This Item

Empirical Formula (Hill Notation):
C4H8O4
CAS Number:
533-50-6
Molecular Weight:
120.10
MDL number:
MFCD00004703
UNSPSC Code:
12352201
PubChem Substance ID:
57651608
NACRES:
NA.25

assay

≥85% (HPLC)

form

liquid

optical activity

[α]/D 12.0±2.0°, c = 2 in H2O (24 h)

impurities

≤23% water

color

light yellow

storage temp.

room temp

SMILES string

OC[C@H](O)C(=O)CO

InChI

1S/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m0/s1

InChI key

UQPHVQVXLPRNCX-VKHMYHEASA-N

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Application

L-(+)-Erythrulose is used as a tanning agent in the cosmetics industry and a source of chiral ethyl ketones used in aldo reaction organic synthesis.

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

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves

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’.

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J Alberto Marco et al.
The Journal of organic chemistry, 68(22), 8577-8582 (2003-10-25)
Both matched and mismatched diastereoselections have been observed in aldol reactions of the B,B-dicyclohexylboron enolate of a protected l-erythrulose derivative with a range of chiral aldehydes. The stereochemical outcome of reactions with alpha-methyl aldehydes can be adequately explained within the
G L Simpson et al.
Biochimica et biophysica acta, 1501(1), 12-24 (2000-03-23)
The degradation of L-ascorbate (AsA) and its primary oxidation products, L-dehydroascorbate (DHA) and 2,3-L-diketogulonate (2, 3-DKG) were studied under physiological conditions. Analysis determined that L-erythrulose (ERU) and oxalate were the primary degradation products of ASA regardless of which compound was
Xingxing Zou et al.
Journal of agricultural and food chemistry, 65(35), 7721-7725 (2017-07-15)
L-erythrose, a rare aldotetrose, possesses various pharmacological activities. However, efficient L-erythrose production is challenging. Currently, L-erythrose is produced by a two-step fermentation process from erythritol. Here, we describe a novel strategy for the production of L-erythrose in Gluconobacter oxydans (G.
Santiago Díaz-Oltra et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(30), 9240-9254 (2008-08-30)
Both matched and mismatched diastereoselection have been observed in aldol reactions of a boron enolate of a protected L-erythrulose derivative with several chiral alpha-fluoro and alpha-amino aldehydes. Strict adherence to the Felkin-Anh model for the respective transition structures does not
Santiago Díaz-Oltra et al.
The Journal of organic chemistry, 70(20), 8130-8139 (2005-11-10)
[Chemical reaction: See text] Both matched and mismatched diastereoselections have been observed in the aldol reactions of a range of chiral aldehydes with the dicyclohexylboron enolate of a chiral ethyl ketone related to L-erythrulose. As was previously observed in the
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