Arabinose

Title: Arabinose
CAS Registry Number: 147-81-9
Additional Names: L-Arabinose; pectin sugar
Molecular Formula: C5H10O5
Molecular Weight: 150.13
Percent Composition: C 40.00%, H 6.71%, O 53.29%
Literature References: Widely distributed in plants, usually in the form of complex polysaccharides. Also in mycobacteria. Isoln from mesquite gum: Anderson, Sands, J. Am. Chem. Soc. 48, 3172 (1926); Org. Synth. coll. vol. I, 16 (2nd ed., 1941); White, J. Am. Chem. Soc. 69, 715 (1947); from western red cedar (Thuja plicata Don., Cupressaceae): Anderson, Erdtman, ibid. 71, 2927 (1949); from sapote gum: White, ibid. 75, 257 (1953); from heartwood of port orford cedar (Chamaecyparis lawsoniana (Murr.) Parl, Cupressaceae): Kritchevsky, Anderson, ibid. 77, 3391 (1955). Structure: Wolfrom, Christman, ibid. 58, 39 (1936). Synthesis: Hough, Jones, J. Chem. Soc. 1951, 1122.
Properties: Orthorhombic bisphenoidal crystals, mp 157-160°. Shows mutarotation. [a]D12 +173° (6 min) ®[a]D20 +105.1° (22½ hrs c = 3). One gram dissolves in about 1 ml water, about 250 ml 90% alc. Ka at 17°, -3.7 ´ 10-13. Reduces Fehling's soln. Forms furfurol on heating to 200° in closed tube also contg water.
Melting point: mp 157-160°
Optical Rotation: [a]D12 +173° (6 min) ®[a]D20 +105.1° (22½ hrs c = 3)
Use: As culture medium for certain bacteria.
Arabitol Arachidic Acid Arachidonic Acid Aramite? Aranidipine

Arabinose
DL-Arabinose.svg
Identifiers
CAS number 147-81-9 YesY, 10323-20-3 (D) YesY, 5328-37-0 (L) YesY
PubChem 5460291
ChemSpider 59687 YesY
EC-number 205-699-8
ChEBI CHEBI:46983 YesY
Jmol-3D images Image 1
Image 2
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 to 165 °C; 327 to 329 °F; 437 to 438 K
Solubility in water Soluble
Hazards
NFPA 704
NFPA 704.svg
1
1
0
Related compounds
Related aldopentoses Ribose
Xylose
Lyxose
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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
Alpha-D-Arabinofuranose.svg
α-D-Arabinofuranose
Beta-D-Arabinofuranose.svg
β-D-Arabinofuranose
Alpha-D-Arabinopyranose.svg
α-D-Arabinopyranose
Beta-D-Arabinopyranose.svg
β-D-Arabinopyranose