3-EtAA
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MedKoo CAT#: 464943

CAS#: 86404-04-8

Description: 3-EtAA is an inhibitor of tyrosinase (IC50s = 16.65 and 29.69 mM for the human and mushroom enzymes, respectively). It also scavenges DPPH radicals (IC50 = 0.032 g/L). Formulations containing 3-O-ethyl-L-ascorbic acid have been used in cosmetic products as skin-lightening agents.


Chemical Structure

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3-EtAA
CAS# 86404-04-8

Theoretical Analysis

MedKoo Cat#: 464943
Name: 3-EtAA
CAS#: 86404-04-8
Chemical Formula: C8H12O6
Exact Mass: 204.0634
Molecular Weight: 204.178
Elemental Analysis: C, 47.06; H, 5.92; O, 47.01

Price and Availability

Size Price Availability Quantity
5.0g USD 210.0 2 Weeks
10.0g USD 350.0 2 Weeks
25.0g USD 580.0 2 Weeks
50.0g USD 840.0 2 Weeks
Bulk inquiry

Synonym: 3-EtAA; 3 EtAA; 3EtAA; 3-O-Ethylascorbic Acid; 3-O-ethyl-L-Ascorbic Acid;

IUPAC/Chemical Name: (R)-5-((S)-1,2-dihydroxyethyl)-4-ethoxy-3-hydroxyfuran-2(5H)-one

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

SMILES Code: OC[C@H](O)[C@@]1(C(OCC)=C(O)C(O1)=O)[H]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 146.93
DMSO 30.0 146.93
Ethanol 30.0 146.93
PBS (pH 7.2) 10.0 48.98

Preparing Stock Solutions

The following data is based on the product molecular weight 204.178 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Zerbinati N, Sommatis S, Maccario C, Di Francesco S, Capillo MC, Rauso R, Herrera M, Bencini PL, Guida S, Mocchi R. The Anti-Ageing and Whitening Potential of a Cosmetic Serum Containing 3-O-ethyl-l-ascorbic Acid. Life (Basel). 2021 Apr 29;11(5):406. doi: 10.3390/life11050406. PMID: 33946734; PMCID: PMC8146548.

2: Iliopoulos F, Chapman A, Lane ME. A comparison of the in vitro permeation of 3-O-ethyl-l-ascorbic acid in human skin and in a living skin equivalent (LabSkin™). Int J Cosmet Sci. 2021 Feb;43(1):107-112. doi: 10.1111/ics.12675. Epub 2020 Dec 25. PMID: 33238056.

3: Hamanaka M, Kanto H, Mikai H, Tanaka H, Ito T, Washizaki K, Ishiko A. A rare case of allergic contact dermatitis caused by 3-O-ethyl-L-ascorbic acid in skin- whitening cosmetics identified under immunosuppressive therapy. Contact Dermatitis. 2020 Dec;83(6):520-521. doi: 10.1111/cod.13652. Epub 2020 Oct 12. PMID: 32617988.

4: Romita P, Foti C, Barlusconi C, Mercurio S, Hansel K, Stingeni L. Allergic contact dermatitis to 3-O-ethyl-L-ascorbic acid: An underrated allergen in cosmetics? Contact Dermatitis. 2020 Jul;83(1):63-64. doi: 10.1111/cod.13528. Epub 2020 Apr 7. PMID: 32208530.

5: Gérard V, Ay E, Graff B, Morlet-Savary F, Galopin C, Mutilangi W, Lalevée J. Ascorbic Acid Derivatives as Potential Substitutes for Ascorbic Acid To Reduce Color Degradation of Drinks Containing Ascorbic Acid and Anthocyanins from Natural Extracts. J Agric Food Chem. 2019 Oct 30;67(43):12061-12071. doi: 10.1021/acs.jafc.9b05049. Epub 2019 Oct 17. PMID: 31588743.

6: Iliopoulos F, Sil BC, Moore DJ, Lucas RA, Lane ME. 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. doi: 10.1016/j.ijpx.2019.100025. PMID: 31517290; PMCID: PMC6733298.

7: Miao F, Su MY, Jiang S, Luo LF, Shi Y, Lei TC. Intramelanocytic Acidification Plays a Role in the Antimelanogenic and Antioxidative Properties of Vitamin C and Its Derivatives. Oxid Med Cell Longev. 2019 May 12;2019:2084805. doi: 10.1155/2019/2084805. PMID: 31214276; PMCID: PMC6535878.

8: Mamodaly M, Dereure O, Raison-Peyron N. A new case of allergic contact dermatitis caused by 3-o-ethyl ascorbic acid in facial antiageing cosmetics. Contact Dermatitis. 2019 Oct;81(4):315-316. doi: 10.1111/cod.13307. Epub 2019 May 24. PMID: 31066077.

9: Fukuchi S , Yagi M , Oguchi-Fujiyama N , Kang J , Kikuchi A . A novel characteristic of salicylate UV absorbers: suppression of diethylhexyl 2,6-naphthalate (Corapan TQ)-photosensitized singlet oxygen generation. Photochem Photobiol Sci. 2019 Jun 12;18(6):1556-1564. doi: 10.1039/c9pp00104b. PMID: 31033968.

10: Shimizu R, Yagi M, Kikuchi A. Suppression of riboflavin-sensitized singlet oxygen generation by l-ascorbic acid, 3-O-ethyl-l-ascorbic acid and Trolox. J Photochem Photobiol B. 2019 Feb;191:116-122. doi: 10.1016/j.jphotobiol.2018.12.012. Epub 2018 Dec 26. PMID: 30605891.

11: Liao WC, Huang YT, Lu LP, Huang WY. Antioxidant Ability and Stability Studies of 3-O-Ethyl Ascorbic Acid, a Cosmetic Tyrosinase Inhibitor. J Cosmet Sci. 2018 Jul/Aug;69(4):233-243. PMID: 30311899.

12: Akutsu K, Kitagawa Y, Yoshimitsu M, Takatori S, Fukui N, Osakada M, Uchida K, Azuma E, Kajimura K. Problems and solutions of polyethylene glycol co- injection method in multiresidue pesticide analysis by gas chromatography-mass spectrometry: evaluation of instability phenomenon in type II pyrethroids and its suppression by novel analyte protectants. Anal Bioanal Chem. 2018 May;410(13):3145-3160. doi: 10.1007/s00216-018-1002-1. Epub 2018 Mar 20. PMID: 29556739.

13: Golonka I, Oleksy M, Junka A, Matera-Witkiewicz A, Bartoszewicz M, Musiał W. Selected Physicochemical and Biological Properties of Ethyl Ascorbic Acid Compared to Ascorbic Acid. Biol Pharm Bull. 2017;40(8):1199-1206. doi: 10.1248/bpb.b16-00967. PMID: 28769001.

14: Victoria-Martínez AM, Mercader-García P. Allergic Contact Dermatitis to 3-o-Ethyl-L-Ascorbic Acid in Skin-lightening Cosmetics. Dermatitis. 2017 Jan/Feb;28(1):89. doi: 10.1097/DER.0000000000000260. PMID: 28002235.

15: Li Y, Dong C, Cun D, Liu J, Xiang R, Fang L. Lamellar Liquid Crystal Improves the Skin Retention of 3-O-Ethyl-Ascorbic Acid and Potassium 4-Methoxysalicylate In Vitro and In Vivo for Topical Preparation. AAPS PharmSciTech. 2016 Jun;17(3):767-77. doi: 10.1208/s12249-015-0353-6. Epub 2015 Sep 8. PMID: 26349686.

16: Numata T, Kobayashi Y, Ito T, Harada K, Tsuboi R, Okubo Y. Two cases of allergic contact dermatitis due to skin-whitening cosmetics. Allergol Int. 2015 Apr;64(2):194-5. doi: 10.1016/j.alit.2014.10.007. Epub 2015 Jan 7. PMID: 25838099.

17: Tai A, Aburada M, Ito H. A simple efficient synthesis and biological evaluation of 3-O-ethylascorbic acid. Biosci Biotechnol Biochem. 2014;78(12):1984-7. doi: 10.1080/09168451.2014.946396. Epub 2014 Aug 15. PMID: 25127395.

18: Yagami A, Suzuki K, Morita Y, Iwata Y, Sano A, Matsunaga K. Allergic contact dermatitis caused by 3-o-ethyl-L-ascorbic acid (vitamin C ethyl). Contact Dermatitis. 2014 Jun;70(6):376-7. doi: 10.1111/cod.12161. PMID: 24846587.

19: Jin S, Miao X. 3-O-Ethyl-l-ascorbic acid. Acta Crystallogr Sect E Struct Rep Online. 2008 Apr 16;64(Pt 5):o860. doi: 10.1107/S1600536808009963. PMID: 21202347; PMCID: PMC2961160.

20: Ogawa K, Futakuchi M, Hirose M, Boonyaphiphat P, Mizoguchi Y, Miki T, Shirai T. Stage and organ dependent effects of 1-O-hexyl-2,3,5-trimethylhydroquinone, ascorbic acid derivatives, n-heptadecane-8-10-dione and phenylethyl isothiocyanate in a rat multiorgan carcinogenesis model. Int J Cancer. 1998 Jun 10;76(6):851-6. doi: 10.1002/(sici)1097-0215(19980610)76:6<851::aid- ijc14>3.0.co;2-5. PMID: 9626352.