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3-O-Ethyl-L-ascorbic acid | 86404-04-8

Product name:3-O-Ethyl-L-ascorbic acid

CAS No:86404-04-8
MF:C8H12O6
MW:204.177283287048
MDL:MFCD09261382
CID:60981
PubChem ID:160871287
Introduction
3-o-ethyl-l-ascorbic acid, a stable vitamin C derivative, is a cosmetic tyrosinase inhibitor with whitening ability. 3-o-ethyl-l-ascorbic acid also has antioxidant ability
Names and Identifiers
  • 3-O-Ethyl-L-ascorbic acid
  • ETHYL ASCORBIC ACID
  • (5r)-5-[(1s)-1,2-dihydroxyethyl]-4-ethoxy-3-hydroxy-5h-furan-2-one
  • 3-O-ETHYLASCORBICACID
  • (5R,1'S)-5-(1,2-Dihydroxy-ethyl)-4-ethoxy-3-hydroxy-5H-furan-2-one
  • (R)-5-((S)-1,2-dihydroxyethyl)-4-ethoxy-3-hydroxyfuran-2(5H)-one
  • (5R)-5-(1,2-dihydroxyethyl)-4-ethoxy-3-hydroxy-2,5-dihydrofuran-2-one
  • (2R)-2-[(1S)-1,2-dihydroxyethyl]-3-ethoxy-4-hydroxy-2H-furan-5-one
  • 3-O-Ethyl Ascorbyl Ether
  • Vc Ethyl Ether
  • Vitamin C Ethyl Ether
  • 3-o-ethyl ascorbic acid
  • 3-O-Ethylascorbic acid
  • L-Ascorbic acid, 3-O-ethyl-
  • 6MW60CB71P
  • 5-(1,2-Dihydroxy-ethyl)-4-ethoxy-3-hydroxy-5H-furan-2-one
  • (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-ethoxy-3-hydroxyfuran-2(5H)-one
  • (5R)-5-((1S)-1,2-Dihydroxyethyl)-4-ethoxy-3-hydroxy-5H-furan-2-one
  • 3-O-Ethyl-L-ascorbicacid
  • A
  • 3-O-Ethyl-L-ascorbic acid (ACI)
  • L-Ascorbic acid 3-O-ethyl ether
  • COS-VCE
  • ENB-VCE
  • VC Ethyl
  • MDL:MFCD09261382
  • InChIKey:ZGSCRDSBTNQPMS-UJURSFKZSA-N
  • 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
  • SMILES:[C@H]([C@H]1OC(=O)C(O)=C1OCC)(O)CO
Chemical and Physical Properties

Computed Properties

  • Exact Mass: 204.18g/mol
  • Surface Charge: 0
  • XLogP3: -1.5
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 6
  • Rotatable Bond Count: 4
  • Monoisotopic Mass: 204.063388g/mol
  • Monoisotopic Mass: 204.063388g/mol
  • Topological Polar Surface Area: 96.2Ų
  • Heavy Atom Count: 14
  • Complexity: 259
  • Isotope Atom Count: 0
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Covalently-Bonded Unit Count: 1

Experimental Properties

  • LogP: -0.92890
  • PSA: 96.22000
  • Refractive Index: 1.555
  • Boiling Point: 551.5°C at 760 mmHg
  • Melting Point: 112.0 to 116.0 deg-C
  • Flash Point: 228.5 °C
  • Color/Form: Pale-yellow to Yellow-brown Solid
  • Specific Rotation: +40 ~ +45° (c=1, MeOH)
  • Density: 1.46
Security Information
  • Hazard Statement:H302-H315-H319-H332-H335
  • Warning Statement:P264; P270; P280; P301+P312; P302+P352; P305+P351+P338; P321; P330; P332+P313; P337+P313; P362; P501
  • Storage Condition:0-10°C
  • Signal Word:Warning
Customs Data
  • HS CODE:2932209090
  • Customs Data:

    China Customs Code:

    2932209090

    Overview:

    2932209090. Other lactones. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Synthetic Circuit

Synthetic Circuit 1

Reaction Conditions
Reference
3-O-alkylascorbic acids as free radical quenchers. 3. Protective effect on coronary occlusion-reperfusion induced arrhythmias in anesthetized rats
Nihro, Yasunori; et al, Journal of Medicinal Chemistry, 1992, 35(9), 1618-23

Synthetic Circuit 2

Reaction Conditions
1.1 Catalysts: Amberlite IR 120 Solvents: Methanol
Reference
Preparation of 3-O-substituted ascorbic acids
, Japan, , ,

Synthetic Circuit 3

Reaction Conditions
1.1 Reagents: Sodium bicarbonate Solvents: Dimethyl sulfoxide ;  6 h, 313 K
1.2 Reagents: Hydrochloric acid Solvents: Water ;  15 min, reflux
Reference
3-O-Ethyl-L-ascorbic acid
Jin, Shu; et al, Acta Crystallographica, 2008, 64(5),

Synthetic Circuit 4

Reaction Conditions
1.1 Solvents: Dimethyl sulfoxide ;  24 h, 50 °C
Reference
A simple efficient synthesis and biological evaluation of 3-O-ethylascorbic acid
Tai, Akihiro; et al, Bioscience, 2014, 78(12), 1984-1987

Synthetic Circuit 5

Reaction Conditions
1.1 Catalysts: Triethylamine Solvents: Ethanol ;  rt
1.2 8 min, reflux
Reference
A facile regioselective synthesis of 3-O-ethyl-L-ascorbic acid
Chen, Bing-bing; et al, Huaxue Shijie, 2012, 53(1), 48-51

Synthetic Circuit 6

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Ethanol ;  1 h, reflux
Reference
Synthesis of 3-O-alkyl-ascorbic acids from L-ascorbic acid in a single step
Kikugawa, Yasuo; et al, Heterocycles, 2005, 66, 579-582
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