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3-O-Ethyl-L-ascorbic acid (vitamin C ethyl ether)

3-O-Ethyl-L-ascorbic acid, a stable vitamin C analogue, is a cosmetic tyrosinase inhibitor (antagonist) with whitening ability.
3-O-Ethyl-L-ascorbic acid (vitamin C ethyl ether)
3-O-Ethyl-L-ascorbic acid (vitamin C ethyl ether) Chemical Structure CAS No.: 86404-04-8
Product category: Tyrosinase
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
3-O-Ethyl-L-ascorbic acid, a stable vitamin C analogue, is a cosmetic tyrosinase inhibitor (antagonist) with whitening ability. 3-O-Ethyl-L-ascorbic acid also has antioxidant capabilities.
3-O-Ethyl-L-ascorbic acid (Vitamin C ethyl ether) is a stable, lipophilic derivative of vitamin C (L-ascorbic acid). It is a cosmetic ingredient known for its tyrosinase inhibitory activity, whitening ability, and antioxidant properties. Unlike L-ascorbic acid, which is highly unstable and prone to oxidation, 3-O-Ethyl-L-ascorbic acid is more stable, allowing for better penetration into the skin. It enters the dermis, directly participates in collagen synthesis, repairs skin cell activity, and increases collagen production. It also has antibacterial and anti-inflammatory effects.
Biological Activity I Assay Protocols (From Reference)
Targets
3-O-Ethyl-L-ascorbic acid targets tyrosinase, the key enzyme in melanin biosynthesis. It is a cosmetic tyrosinase inhibitor that inhibits the formation of melanin. By inhibiting tyrosinase, the compound reduces melanin production, leading to skin whitening and lightening of hyperpigmented areas. It also targets collagen synthesis pathways, promoting skin repair and elasticity.
ln Vitro
3-O-Ethyl-L-ascorbic acid demonstrates potent in vitro tyrosinase inhibitory activity. It inhibits melanin formation and restores melanin to a colorless state. The compound has strong antibacterial and anti-inflammatory effects. It effectively removes freckles, whitens skin, improves dull skin, and endorses skin elasticity by promoting collagen synthesis and repairing skin cell activity.
ln Vivo
In vivo activity data for 3-O-Ethyl-L-ascorbic acid are not extensively documented. Its topical application in cosmetic formulations suggests that it is effective in vivo for skin whitening and improving skin condition. It enters the dermis and directly participates in collagen synthesis. Further in vivo studies are needed to fully characterize its efficacy and pharmacokinetic profile.
Enzyme Assay
The in vitro enzyme assay for 3-O-Ethyl-L-ascorbic acid involves measuring its inhibition of tyrosinase activity. Mushroom tyrosinase is commonly used as a model enzyme. The assay typically uses L-DOPA as a substrate, and the formation of dopachrome is monitored spectrophotometrically at 475 nm. 3-O-Ethyl-L-ascorbic acid is incubated with the enzyme and substrate at various concentrations. The IC50 value is determined by fitting the inhibition data to a dose-response curve.
Cell Assay
In vitro cellular assays for 3-O-Ethyl-L-ascorbic acid typically use B16 melanoma cells or human melanocytes to assess its effects on melanogenesis. Cells are treated with the compound at various concentrations. Melanin content is measured spectrophotometrically. Tyrosinase activity is assessed by measuring the oxidation of L-DOPA in cell lysates. Collagen synthesis can be assessed in fibroblasts by measuring collagen production.
Animal Protocol
In vivo studies for 3-O-Ethyl-L-ascorbic acid are typically conducted in human subjects as part of cosmetic efficacy studies. The compound is applied topically in formulations. Skin lightening, reduction in pigmentation, and improvement in skin elasticity and hydration are assessed using clinical scoring, colorimetry, and biophysical measurements.
ADME/Pharmacokinetics
The pharmacokinetic properties of 3-O-Ethyl-L-ascorbic acid are characterized by its stability and skin penetration. As a lipophilic derivative of vitamin C, it has better skin permeability than L-ascorbic acid. It enters the dermis and is available for collagen synthesis. Its metabolic fate and systemic absorption are not extensively documented.
Toxicity/Toxicokinetics
Toxicological data for 3-O-Ethyl-L-ascorbic acid are limited. As a cosmetic ingredient, it is generally considered safe for topical use. It has antibacterial and anti-inflammatory effects. Standard safety assessments for cosmetic ingredients, including skin irritation and sensitization tests, have likely been performed. Further toxicological studies would be required for systemic use.
References

[1]. Antioxidant Ability and Stability Studies of 3- O-Ethyl Ascorbic Acid, a Cosmetic Tyrosinase Inhibitor. J Cosmet Sci. Jul/Aug 2018;69(4):233-243.

[2]. 3-O-ethyl-l-ascorbic acid: Characterisation and investigation of single solvent systems for delivery to the skin. Int J Pharm X. 2019 Jul 19;1:100025.

Additional Infomation
3-O-ethyl ascorbic acid is a butenolactone.
See also: ... View more ...
3-O-Ethyl-L-ascorbic acid (Vitamin C ethyl ether) is a stable, lipophilic vitamin C derivative used in cosmetics for skin whitening, antioxidant protection, and collagen synthesis. It inhibits tyrosinase activity and melanin formation. The compound has antibacterial and anti-inflammatory effects. No clinical trials or regulatory approvals have been reported for this compound as a drug.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H12O6
Molecular Weight
204.18
Exact Mass
204.063
CAS #
86404-04-8
PubChem CID
150736
Appearance
White to off-white solid powder
Density
1.5±0.1 g/cm3
Boiling Point
551.5±50.0 °C at 760 mmHg
Melting Point
112.0 to 116.0 °C
Flash Point
228.5±23.6 °C
Vapour Pressure
0.0±3.4 mmHg at 25°C
Index of Refraction
1.555
LogP
-1.8
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
4
Heavy Atom Count
14
Complexity
259
Defined Atom Stereocenter Count
2
SMILES
CCOC1=C(C(=O)O[C@@H]1[C@H](CO)O)O
InChi Key
ZGSCRDSBTNQPMS-UJURSFKZSA-N
InChi Code
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
Chemical Name
(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-ethoxy-4-hydroxy-2H-furan-5-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O: 100 mg/mL (489.76 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (489.76 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.8976 mL 24.4882 mL 48.9764 mL
5 mM 0.9795 mL 4.8976 mL 9.7953 mL
10 mM 0.4898 mL 2.4488 mL 4.8976 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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