Skip to content
D-threose

Structure via PubChem · Public domain (PubChem)

EntityQ423233· pop 33· linked from 122 articles

Also known as D-(-)-Threose

Threose is a four-carbon monosaccharide with molecular formula C4H8O4. It has a terminal aldehyde group, rather than a ketone, in its linear chain and so is considered part of the aldose family of monosaccharides. The threose name can be used to refer to both the - and -stereoisomers and more generally to the racemic mixture (/L-, equal parts D- and L-) as well as to the more generic threose structure (absolute stereochemistry unspecified).

Chemical data

Formula
C4H8O4
Molecular weight
120.1 g/mol
IUPAC name
(2S,3R)-2,3,4-trihydroxybutanal
SMILES
C([C@H]([C@@H](C=O)O)O)O
InChIKey
YTBSYETUWUMLBZ-QWWZWVQMSA-N
XLogP
-2.2
Polar surface area
77.8 Ų
H-bond donors
3
H-bond acceptors
4
Formal charge
0

via PubChem

Wikidata facts

Mass
120.042
Show 4 more facts
Commons category
Threose
chemical formula
C₄H₈O₄
canonical SMILES
C(C(C(C=O)O)O)O
isomeric SMILES
C([C@H]([C@@H](C=O)O)O)O
Sources (2)

via Wikidata · CC0

~1 min read

Article

2 sections
Contents
  • See also
  • References

Threose is a four-carbon monosaccharide with molecular formula C4H8O4. It has a terminal aldehyde group, rather than a ketone, in its linear chain and so is considered part of the aldose family of monosaccharides. The threose name can be used to refer to both the - and -stereoisomers and more generally to the racemic mixture (/L-, equal parts D- and L-) as well as to the more generic threose structure (absolute stereochemistry unspecified).

The prefix "threo-" which derives from threose (and "erythro-" from a corresponding diastereomer erythrose) offer a useful way to describe general organic structures with adjacent chiral centers, where "the prefixes... designate the relative configuration of the centers". As is depicted in a Fischer projection of -threose, the adjacent substituents will have a syn orientation in the isomer referred to as "threo", and are anti in the isomer referred to as "erythro".

Gallery (3)

Connections

Categories