Arabinose

Arabinose
IUPAC name Arabinose
Other names Pectinose
Identifiers
CAS number	147-81-9 Y, 10323-20-3 (D) Y, 5328-37-0 (L) Y
PubChem	5460291
ChemSpider	59687 Y
EC-number	205-699-8
ChEBI	CHEBI:46983 Y
Jmol-3D images	Image 1 Image 2
SMILES O=C[C@@H](O)[C@H](O)[C@H](O)CO C([C@H]([C@H]([C@@H](C=O)O)O)O)O
InChI InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1 Y Key: PYMYPHUHKUWMLA-WDCZJNDASA-N Y InChI=1/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1 Key: PYMYPHUHKUWMLA-WDCZJNDABW
Properties[1]
Molecular formula	C5H10O5
Molar mass	150.13 g mol−1
Appearance	Colorless crystals as prisms or needles
Density	1.585 g/cm3 (20 ºC)
Melting point	164-165 °C, 437-438 K, 327-329 °F
Solubility in water	Soluble
Related compounds
Related aldopentoses	Ribose Xylose Lyxose
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Arabinose is an aldopentose – a monosaccharide containing five carbon atoms, and including an aldehyde (CHO) functional group.

For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous to D-glyceraldehyde.^{[note 1]} However, L-arabinose is in fact more common than D-arabinose in nature and is found in nature as a component of biopolymers such as hemicellulose and pectin. The L-arabinose operon is a very important operon in molecular biology and bioengineering.

A classic method for the organic synthesis of arabinose from glucose is the Wohl degradation.^[2]

D-Arabinose
α-D-Arabinofuranose	β-D-Arabinofuranose
α-D-Arabinopyranose	β-D-Arabinopyranose

Etymology

Arabinose gets its name from gum arabic, from which it was first isolated.^[3]

Use

Arabinose is used as a culture medium for certain bacteria.

Notes

1. ^ For sugars, the D/L nomenclature does not refer to the molecule's optical rotation properties but to its structural analogy to glyceraldehyde.

References

1. ^ Weast, Robert C., ed (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-110. ISBN 0-8493-0462-8. 
2. ^ Braun, Géza (1940), "D-Arabinose", Org. Synth. 20: 14, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV3P0101 ; Coll. Vol. 3: 101 
3. ^ Merriam Webster Dictionary