3-EtAA | CAS#86404-04-8 | Tyrosinase inhibitor

MedKoo Cat#: 464943 | Name: 3-EtAA

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

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: 204.18

Elemental Analysis: C, 47.06; H, 5.92; O, 47.01

Price and Availability

Size	Price	Availability
5g	USD 250.00	2 Weeks
10g	USD 350.00	2 Weeks
25g	USD 550.00	2 Weeks

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Related CAS #

No Data

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

More Info

Instruction

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	Solvent	mg/mL	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

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 204.18 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.

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

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.