D-ERYTHRONOLACTONE Chemical Properties

Melting point:

100-102 °C(lit.)

Boiling point:

140.59°C (rough estimate)

Density 

1.0887 (rough estimate)

refractive index 

-71 ° (C=1, H2O)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

12.34±0.40(Predicted)

color 

White to Off-White

optical activity

[α]20/D 71°, c = 1 in H2O

BRN 

81073

CAS DataBase Reference

15667-21-7(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29322090

MSDS

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

D-ERYTHRONOLACTONE Usage And Synthesis

Chemical Properties

D-ERYTHRONOLACTONE is white to light yellow crystal powde

Uses

D-ERYTHRONOLACTONE is a chiral synthon used for the synthesis of certain natural products such as the leukotrienes

Uses

D-erythrono-1,4-lactone is a potential substrates of dihydroxy acid dehydratase.

Uses

A chiral synthon used for the synthesis of certain natural products such as the leukotrienes.

Definition

ChEBI: Erythrono-1,4-lactone is a butan-4-olide that is dihydrofuran-2-one substituted at C-3 and C-4 by hydroxy groups (the 3R,4R-diastereomer). It is a butan-4-olide and a diol.

Synthesis

Isoascorbic acid (17.6 g, 0.1 mol) was used as the raw material, which was dissolved in 250 mL of water and the solution was cooled to 0-6 °C. Anhydrous sodium carbonate powder (21.2 g, 0.2 mol) was added to the reaction flask in batches under stirring conditions. After the addition was completed, 30% hydrogen peroxide solution (22 mL) was added slowly and the internal temperature was increased from 6°C to 19°C during the reaction. Subsequently, the reaction mixture was placed in an ice bath and stirring was continued for 5 min, at which time the internal temperature increased to 27 °C. The reaction solution was heated to 42 °C and maintained at this temperature with stirring for 30 minutes. Zinc powder (1.0 g, 0.015 mol) was added to the reaction mixture and the reaction was subsequently quenched with excess hydrogen peroxide until the potassium iodide starch test paper was negative. The pH of the reaction solution was adjusted to 1.0 with 6 N hydrochloric acid. the reaction solution was concentrated to a small volume under reduced pressure at 50 °C to precipitate a white solid. Extraction was carried out with ethyl acetate (150 mL x 3), the organic phases were combined and concentrated to 200 mL (10-15 v/v). The concentrate was cooled to 15-25 °C and stirred for 5 to 8 hours to induce the precipitation of a large amount of white solid. Finally, after filtration and drying, 8.26 g (3R,4R)-3,4-dihydroxydihydrofuran-2(3H)-one was obtained in 70% yield.

Purification Methods

Recrystallise it from EtOAc (20 parts) or isoPrOH (3 parts). [Baker & MacDonald J Am Chem Soc 82 230 1960, Glattfeld & Forbrich J Am Chem Soc 56 1209 1934, Weidenhagen & Wegner Chem Ber 72 2010 1939, Musich & Rapoport J Am Chem Soc 100 4865 1978, Beilstein 18/2 V 457.]

References

[1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 7, p. 1013 - 1016
[2] Patent: CN105503903, 2016, A. Location in patent: Paragraph 0270; 0271; 0272; 0273

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