Arabinose

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Arabinose
DL-Arabinose.svg
Identifiers
CAS number147-81-9 YesY, 10323-20-3 (D) YesY, 5328-37-0 (L) YesY
PubChem5460291
ChemSpider59687 YesY
EC-number205-699-8
ChEBICHEBI:46983 YesY
Jmol-3D imagesImage 1
Image 2
Properties[1]
Molecular formulaC5H10O5
Molar mass150.13 g mol−1
AppearanceColorless crystals as prisms or needles
Density1.585 g/cm3 (20 ºC)
Melting point164 to 165 °C (327 to 329 °F; 437 to 438 K)
Solubility in waterSoluble
Hazards
NFPA 704
Related compounds
Related aldopentosesRibose
Xylose
Lyxose
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references
 
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Arabinose
DL-Arabinose.svg
Identifiers
CAS number147-81-9 YesY, 10323-20-3 (D) YesY, 5328-37-0 (L) YesY
PubChem5460291
ChemSpider59687 YesY
EC-number205-699-8
ChEBICHEBI:46983 YesY
Jmol-3D imagesImage 1
Image 2
Properties[1]
Molecular formulaC5H10O5
Molar mass150.13 g mol−1
AppearanceColorless crystals as prisms or needles
Density1.585 g/cm3 (20 ºC)
Melting point164 to 165 °C (327 to 329 °F; 437 to 438 K)
Solubility in waterSoluble
Hazards
NFPA 704
Related compounds
Related aldopentosesRibose
Xylose
Lyxose
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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

Etymology[edit]

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

Use[edit]

Arabinose is used as a culture medium for certain bacteria.

Notes[edit]

  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[edit]

  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 ; Coll. Vol. 3: 101 
  3. ^ Merriam Webster Dictionary