L(+)-Gulonic acid gamma-lactone Chemical Properties

Melting point:

187-190 °C(lit.)

alpha 

54.5 º (c=2, water 57.5 ºC)

Boiling point:

230.35°C (rough estimate)

Density 

1.3253 (rough estimate)

refractive index 

56 ° (C=2, H2O)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Sparingly)

pka

12.06±0.60(Predicted)

form 

Viscous Solution

color 

White to Off-white

optical activity

[α]19/D +55°, c = 4 in H2O

Water Solubility 

Soluble in water

BRN 

83002

InChI

InChI=1/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/s3

InChIKey

SXZYCXMUPBBULW-QICJDPMJNA-N

SMILES

[C@H]1([C@@H](O)CO)OC(=O)[C@@H](O)[C@H]1O |&1:0,1,8,10,r|

CAS DataBase Reference

1128-23-0(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29400090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

L(+)-Gulonic acid gamma-lactone Usage And Synthesis

Chemical Properties

White Solid

Uses

L-Gulono-1,4-lactone is a precursor in the biosynthesis of ascorbic acid, one of the many forms of Vitamin C.

Definition

ChEBI: L-gulono-1,4-lactone is the furanose form of gulonolactone having L-configuration. It has a role as a human metabolite and a mouse metabolite. It is functionally related to a L-gulonic acid.

Synthesis

The general procedure for the synthesis of L-gulosonic acid-γ-lactone from L-ascorbic acid was as follows: 10% Pd/C catalyst (8.3 g) was added to a solution of L-ascorbic acid (83.9 g, 0.477 mol) in water (600 mL). The reaction mixture was placed in a Parr hydrogenator and hydrogenated for 62 hours at 48 psi hydrogen pressure and 18°C. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated under vacuum to afford L-gulosonic acid-γ-lactone (81.0 g, 96% yield) as an off-white solid. The resulting solid was dried in a vacuum oven at 50 °C for 18 h. The melting point was measured to be 182-184 °C.

References

[1] Journal of Organic Chemistry, 1981, vol. 46, # 14, p. 2976 - 2977
[2] Patent: US2004/54172, 2004, A1
[3] Patent: US2003/232889, 2003, A1. Location in patent: Page/Page column 12
[4] Synlett, 2017, vol. 28, # 8, p. 970 - 972
[5] Tetrahedron Asymmetry, 1996, vol. 7, # 9, p. 2711 - 2720

L(+)-Gulonic acid gamma-lactone(1128-23-0)Related Product Information

• CDH
• Dodecyl acrylate
• 4-Hexanolide
• Polycaprolactone
• L-GULOSE
• D-(-)-Gulonic acid gamma-lactone
• 5,6-O-Isopropylidene-L-gulonic acid-1,4-lactone
• RARECHEM AL BP 0349
• 6,3-GLUCURONOLACTONE ACETONIDE
• D-Glucurono-6,3-lactone acetonide
• L(+)-Gulonic acid gamma-lactone
• 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone
• 2,3-DI-O-ACETYL-5,6-O-ISOPROPYLIDENE-L-GULONO-1,4-LACTONE
• 2,3:5,6-Di-O-isopropylidene-L-gulonolactone