Altrose

Altrose
Names
	Preferred IUPAC name Altrose
	Systematic IUPAC name (2S,3R,4R)-2,3,4,5,6-Pentahydroxyhexanal
Identifiers
CAS Number	1990-29-0 (D) ; 1949-88-8 (L) ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:28385 (D); CHEBI:63421 (L);
ChemSpider	389851 ;
KEGG	C06464 (D);
PubChem CID	441032 (D); 10219674 (L);
UNII	5PLN1O36FF (D) ;
	InChI InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4?,5+,6-/m1/s1 Key: GZCGUPFRVQAUEE-ZPQYLTHOSA-N ; InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5+,6?/m1/s1; InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5+,6?/m1/s1 Key: WQZGKKKJIJFFOK-RSVSWTKNSA-N;
	SMILES OCC(O)[C@@H](O)[C@@H](O)[C@H](O)C=O; O[C@@H]1[C@H](O)[C@H](OC(O)[C@H]1O)CO;
Properties
Chemical formula	C6H12O6
Molar mass	180.156 g·mol−1
Melting point	103 to 105 °C (217 to 221 °F; 376 to 378 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Altrose is an aldohexose sugar. D-Altrose is an unnatural monosaccharide. It is soluble in water and practically insoluble in methanol. However, L-altrose has been isolated from strains of the bacterium Butyrivibrio fibrisolvens.^[1]

Altrose is a C-3 epimer of mannose. The ring conformation of α-altropyranoside is flexible compared to most other aldohexopyranosides, with idose as exception. In solution different derivatives of altrose have been shown to occupy both ⁴C₁, ^OS₂ and ¹C₄-conformations.^[2]

Haworth projections of various forms of D-altrose

References

^ US patent 4966845, Stack; Robert J., "Microbial production of L-altrose", issued 1990-10-30, assigned to Government of the United States of America, Secretary of Agriculture
^ Immel, Stefan; Fujita, Kahee; Lichtenthaler, Frieder W. (1999). "Solution Geometries and Lipophilicity Patterns ofα-Cycloaltrin". Chemistry - A European Journal. 5 (11): 3185–3192. doi:10.1002/(SICI)1521-3765(19991105)5:11<3185::AID-CHEM3185>3.0.CO;2-W. ISSN 0947-6539.

[1] US patent 4966845, Stack; Robert J., "Microbial production of L-altrose", issued 1990-10-30, assigned to Government of the United States of America, Secretary of Agriculture

[ImmelFujita1999-2] Immel, Stefan; Fujita, Kahee; Lichtenthaler, Frieder W. (1999). "Solution Geometries and Lipophilicity Patterns ofα-Cycloaltrin". Chemistry - A European Journal. 5 (11): 3185–3192. doi:10.1002/(SICI)1521-3765(19991105)5:11<3185::AID-CHEM3185>3.0.CO;2-W. ISSN 0947-6539.

[1]

[2]

Names


Preferred IUPAC name Altrose
Systematic IUPAC name (2S,3R,4R)-2,3,4,5,6-Pentahydroxyhexanal
Identifiers
CAS Number	1990-29-0 (D) 1949-88-8 (L)
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:28385 (D) CHEBI:63421 (L)
ChemSpider	389851
KEGG	C06464 (D)
PubChem CID	441032 (D) 10219674 (L)
UNII	5PLN1O36FF (D)
InChI InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4?,5+,6-/m1/s1 Key: GZCGUPFRVQAUEE-ZPQYLTHOSA-N InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5+,6?/m1/s1 InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5+,6?/m1/s1 Key: WQZGKKKJIJFFOK-RSVSWTKNSA-N
SMILES OCC(O)[C@@H](O)[C@@H](O)[C@H](O)C=O O[C@@H]1[C@H](O)[C@H](OC(O)[C@H]1O)CO
Properties
Chemical formula	C₆H₁₂O₆
Molar mass	180.156 g·mol⁻¹
Melting point	103 to 105 °C (217 to 221 °F; 376 to 378 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).