Sorbose

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 450955931

| ImageFileL1 = L-sorbose_Fischer.png

| ImageSizeL1 = 75px

| ImageFileR1 = sorbose.png

| ImageSizeR1 = 150px

| IUPACName = L-xylo-Hex-2-ulose

| OtherNames = Sorbinose
L-xylo-Hexulose

| SystematicName = (3S,4R,5S)-1,3,4,5,6-Pentahydroxyhexan-2-one

| Section1 = {{Chembox Identifiers

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo=87-79-6

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = NV2001607Y

|PubChem=6904

|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

|ChemSpiderID = 6638

|InChI = 1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6+/m0/s1

|InChIKey = BJHIKXHVCXFQLS-OTWZMJIIBK

|StdInChI_Ref = {{stdinchicite|changed|chemspider}}

|StdInChI = 1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6+/m0/s1

|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

|StdInChIKey = BJHIKXHVCXFQLS-OTWZMJIISA-N

|SMILES=C([C@@H]([C@H]([C@@H](C(=O)CO)O)O)O)O

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| Section2 = {{Chembox Properties

|Properties_ref = Merck Index, 12th Edition, 8874

|C=6 | H=12 | O=6

|Appearance=white solid

|Density=1.65 g/cm3 (15 °C)

|MeltingPtC=165

|Solubility=Highly Soluble

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Sorbose is a ketose belonging to the group of sugars known as monosaccharides. It has a sweetness that is equivalent to sucrose (table sugar). The commercial production of vitamin C (ascorbic acid) often begins with sorbose. L-Sorbose is the configuration of the naturally occurring sugar. It can be prepared from inexpensive O-benzylglucose.

Synthesis

Under conditions employed for a Meerwein-Ponndorf-Verley reduction, the tetra-O-benzyl aldose converts to tetra-O-benzylsorbose. Hydrogenolysis removes the four benzyl groups, leaving sorbose.{{cite journal |doi=10.1021/acs.chemrev.5b00104 |title=Synthesis of l-Hexoses |year=2015 |last1=Frihed |first1=Tobias Gylling |last2=Bols |first2=Mikael |last3=Pedersen |first3=Christian Marcus |journal=Chemical Reviews |volume=115 |issue=9 |pages=3615–3676 |pmid=25893557 }}

References

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Category:Ketohexoses