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87-79-6

87-79-6 Structure

87-79-6 Structure
IdentificationMore
[Name]

L-(-)-SORBOSE
[CAS]

87-79-6
[Synonyms]

L-SOR
L-(-)-SORBOSE
L-SORBOSE
SORBIN
SORBOSE
SORBOSE(L-)
Esorben
Hex-2-ulose
l-1,2,3,4,5,6-pentahydroxyhexan-2-one
l-1,3,4,5,6-Pentahydroxyhexan-2-one
l-Sorbinose
l-sorbos
l-Xylo-2-hexulose
l-xylo-hexulose
Sorbinose
L-(−
)-Sorbose
L(-)-SORBOSE, FOR BIOTECHNOLOGICAL PURPO SES
L(-)SorboseForBiochemistry
2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Foic acid
[EINECS(EC#)]

201-771-8
[Molecular Formula]

C6H12O6
[MDL Number]

MFCD00151097
[Molecular Weight]

180.16
[MOL File]

87-79-6.mol
Chemical PropertiesBack Directory
[Appearance]

White to off-white crystalline powder or crystals
[Melting point ]

163-165 °C
[alpha ]

-43 º (C=5% IN H2O)
[Boiling point ]

232.96°C (rough estimate)
[density ]

1.65 g/cm
[refractive index ]

-43 ° (C=1, H2O)
[storage temp. ]

Inert atmosphere,2-8°C
[solubility ]

H2O: 0.1 g/mL, clear, colorless to very faintly yellow
[form ]

Crystalline Powder or Crystals and Chunks
[pka]

pKa (17.5° ): 11.55
[color ]

White to off-white
[Odor]

Odorless
[Optical Rotation]

[α]20/D 43±2°, c = 5% in H2O
[Water Solubility ]

354.8g/L(17 ºC)
[Merck ]

8726
[BRN ]

1724554
[LogP]

-1.029 (est)
[CAS DataBase Reference]

87-79-6(CAS DataBase Reference)
[NIST Chemistry Reference]

L-Sorbose(87-79-6)
[EPA Substance Registry System]

87-79-6(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

3
[RTECS ]

WG3195025
[TSCA ]

TSCA listed
[HS Code ]

29400090
[Hazardous Substances Data]

87-79-6(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

D-Sorbitol-->L-Tagatose-->L-(+)-THREOSE-->L-IDITOL-->L-GULOSE-->L-(-)-IDOSE-->D(-)-Fructose-->β-Hydroxypyruvic acid-->D-Serine-->L-Glyceraldehyde
[Preparation Products]

2,2-DIMETHYL-4-PHENYL-1,3-DIOXOLANE-->L-xylo-hex-2-ulosonic acid-->2-Hydroxypropanoic acid-->D(-)-Fructose
Hazard InformationBack Directory
[Chemical Properties]

White to off-white crystalline powder or crystals
[Uses]

L-Sorbose is used as a starting reagent for the commercial biosynthesis of ascorbic acid (vitamin C).
[Uses]

In the manufacture of vitamin C (accounts for nearly 1000 tons of ascorbic acid produced every year). For conversion of L-sorbose to 2-keto-L-gulonic acid see Reichstein, Grüssner, Helv. Chim. Acta 17, 311 (1934).
[Uses]

L-Sorbose is a low molecular weight naturally occurring monosaccharide carbohydrate molecule. It has sweetness that is nearly equivalent to that of sucrose. This is a labeled analog.
[Definition]

ChEBI: Keto-L-sorbose is a L-sorbose. It is an enantiomer of a keto-D-sorbose.
[Biochem/physiol Actions]

The L enatiomer of sorbose, a ketohexose monosaccharide.
[Synthesis]

D(-)-Fructose

57-48-7

2-Hydroxypropanoic acid

849585-22-4

D-HAMAMELOSE

4573-78-8

L-(-)-SORBOSE

87-79-6

D-tagatose

87-81-0

D-PSICOSE

551-68-8

1,3-Dihydroxyacetone

96-26-4

DL-GLYCERALDEHYDE

56-82-6

The target compounds were synthesized from D-fructose by the following steps: 2-hydroxypropanoic acid, D-witch hazel sugar, (3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-one, (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one, (3R,4R,5R)-1,3,4,5,6-pentahydroxyhexan-2-one, 1 ,3-dihydroxyacetone and DL-glyceraldehyde. This was done as follows: the D-fructose was reacted with MoO3 in water at 100 °C for 4 h. After completion of the reaction, the fructose-containing grades were separated by appropriate methods. Analysis using 1H NMR spectroscopy (shown in Fig. 8) confirmed the presence of sorbose in the separated grades.

[storage]

Store at -20°C
[References]

[1] Patent: US2017/15614, 2017, A1. Location in patent: Page/Page column 2; 13-14
Spectrum DetailBack Directory
[Spectrum Detail]

L-(-)-SORBOSE(87-79-6)MS
L-(-)-SORBOSE(87-79-6)1HNMR
L-(-)-SORBOSE(87-79-6)13CNMR
L-(-)-SORBOSE(87-79-6)IR1
L-(-)-SORBOSE(87-79-6)IR2
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

L(-)-Sorbose, 98%(87-79-6)
[Sigma Aldrich]

87-79-6(sigmaaldrich)
[TCI AMERICA]

L-(-)-Sorbose,>98.0%(LC)(87-79-6)
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