3-O-Ethyl-L-ascorbic acid Chemical Properties

Melting point:

112.0 to 116.0 °C

Boiling point:

551.5±50.0 °C(Predicted)

Density 

1.46±0.1 g/cm3(Predicted)

vapor pressure 

0-0Pa at 20-25℃

storage temp. 

Sealed in dry,2-8°C

solubility 

Methanol (Slightly), Water (Slightly)

form 

Solid

pka

8.89±0.40(Predicted)

color 

White to Off-White

optical activity

46.1°(C=0.01 g/mL, MeOH, 20°C, 589nm)

InChI

InChI=1S/C8H12O6/c1-2-13-7-5(11)8(12)14-6(7)4(10)3-9/h4,6,9-11H,2-3H2,1H3/t4-,6+/m0/s1

InChIKey

ZGSCRDSBTNQPMS-UJURSFKZSA-N

SMILES

O(CC)C1=C(O)C(=O)O[C@@H]1[C@H](CO)O

LogP

-0.8--0.64 at 20-25℃ and pH7

Surface tension

69-72.4mN/m at 1g/L and 20℃

Safety Information

HS Code 

2936.27.0000

3-O-Ethyl-L-ascorbic acid Usage And Synthesis

Description

3-O-Ethyl-L-ascorbic acid is a product of ascorbic acid-3-O-ethylation. It has a simple molecular structure and is easily absorbed by the skin. After entering the dermis through the stratum corneum of the skin, it is easily decomposed by the biological enzymes in the human body. The effect of ascorbic acid effectively solves the fat solubility problem of ascorbic acid, and is widely used in cosmetics as a whitening agent and antioxidant.

Uses

3-O-Ethyl-L-ascorbic Acid could be a useful stabilizing agent for a para-hydroxyacetophenone solution. It could be a useful stabilizing agent for a para-hydroxyacetophenone solution.

Definition

ChEBI: 3-O-ethyl-l-ascorbic acid (EA) is a butenolide. It is an l-ascorbic acid derivative with an ethyl group at the third carbon position. 

Health effects

3-O-ethyl-L-ascorbic acid improves the molecules' stability and its transportation efficacy to the skin, being absorbed faster and better. Additionally, it is less irritating to the skin. Cosmetic case studies demonstrate that they have skin brightening, collagen stimulating, and antioxidant properties.

Mechanism of action

VC ethyl ether penetrates the stratum corneum to reach the melanocytes in the basal layer, inhibits tyrosinase activity, inhibits the formation of melanin, and restores melanin to colorless, thereby effectively whitening the skin. And Chemicalbook and VC ethyl ether can directly participate in the synthesis of collagen and repair skin cell activity after entering the dermis, increasing collagen, so that the skin becomes full and elastic, making the skin delicate and smooth.

Synthesis

The above 3-O-ethyl-5,6-O-isopropylideneascorbic acid 40g dissolved in 200ml of ethanol. 10g of cation-exchange resin was added and was refluxed for 2 hours. The catalyst was removed by an ion exchange resin and concentrated under reduced pressure. After drying, with ethyl acetate: hexane (3: 1) crystallization. After drying, obtained 33.3g 3-O-ethylascorbic acid, yield 94%. It was recrystallized in 100mL ethyl acetate giving 30.6g, yield 87%, mp: 112-114??C.

References

[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 9, p. 1618 - 1623
[2] Patent: CN105367524, 2016, A. Location in patent: Paragraph 0035; 0038
[3] Patent: WO2008/44809, 2008, A1. Location in patent: Page/Page column 10
[4] Patent: US2010/56809, 2010, A1. Location in patent: Page/Page column 3
[5] Patent: WO2008/44809, 2008, A1. Location in patent: Page/Page column 10-11

3-O-Ethyl-L-ascorbic acid(86404-04-8)Related Product Information

• 4-Ethoxyphenol
• Ethyl formate
• Erythorbic Acid
• Ethyl acrylate
• Ethylparaben
• Ethylbenzene
• tert-Butyl ethyl ether
• Calcium ascorbate dihydrate
• ASCORBATE OXIDASE
• Furan
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• Ethoxyquin
• Ethyl acetate
• Ethanol
• CHLOROPHOSPHONAZO III
• acetic acid, triethoxy-, ethyl ester
• Ascorbic Acid
• 1,1'-Thiobisethane