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MedKoo Cat#: 412275 | Name: Ecamsule
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Description:

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

Ecamsule is an organic compound which is added to many sunscreens to filter out UVA rays. It is a benzylidene camphor derivative, many of which are known for their excellent photostability. Abreviated as TDSA; FDA approved 2006 as component of Anthelios SX along with avobenzone and octocrylene.

Chemical Structure

Ecamsule
Ecamsule
CAS#92761-26-7 (free)

Theoretical Analysis

MedKoo Cat#: 412275

Name: Ecamsule

CAS#: 92761-26-7 (free)

Chemical Formula: C28H38O8S2

Exact Mass: 566.2008

Molecular Weight: 566.72

Elemental Analysis: C, 59.34; H, 6.76; O, 22.58; S, 11.31

Price and Availability

Size Price Availability Quantity
1g USD 350.00 2 Weeks
5g USD 950.00 2 Weeks
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Related CAS #
92761-26-7 (free) 92841-53-7 (ditriethanolamine)
Synonym
Ecamsule; Mexoryl SX; Mexoryl; NSC-760054; NSC760054; NSC 760054
IUPAC/Chemical Name
(E-E )-3,3'-(1,4-Phenylenedimethylidene)bis(2-oxobornane-10-sulfonic acid)
InChi Key
XDLGATIAMPGERU-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H38O8S2/c1-25(2)21-9-11-27(25,15-37(31,32)33)23(29)19(21)13-17-5-7-18(8-6-17)14-20-22-10-12-28(24(20)30,26(22,3)4)16-38(34,35)36/h5-8,19-22H,9-16H2,1-4H3,(H,31,32,33)(H,34,35,36)
SMILES Code
CC1(C)C2(CS(=O)(O)=O)CCC1C(CC3=CC=C(CC(C4CCC5(CS(=O)(O)=O)C4(C)C)C5=O)C=C3)C2=O
Appearance
Solid powder
Purity
>95% (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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Although there are a few different UV absorbers with the trade name Mexoryl, only two of them are widely used where approved. Mexoryl SX (water-soluble) and Mexoryl XL (INCI Drometrizole trisiloxane, oil-soluble). Together they show a synergistic effect in protection. The patents are held by L'Oréal. Sunscreens containing ecamsule are exclusive to L'Oréal and its brands.

Preparing Stock Solutions

The following data is based on the product molecular weight 566.72 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
1: Matta MK, Zusterzeel R, Pilli NR, Patel V, Volpe DA, Florian J, Oh L, Bashaw E, Zineh I, Sanabria C, Kemp S, Godfrey A, Adah S, Coelho S, Wang J, Furlong LA, Ganley C, Michele T, Strauss DG. Effect of Sunscreen Application Under Maximal Use Conditions on Plasma Concentration of Sunscreen Active Ingredients: A Randomized Clinical Trial. JAMA. 2019 Jun 4;321(21):2082-2091. doi: 10.1001/jama.2019.5586. PMID: 31058986; PMCID: PMC6549296. 2: Hofer S, Stonig M, Wally V, Hartmann A, Fuchs D, Hermann M, Paparella M, Ganzera M, Gostner JM. Contradictory effects of chemical filters in UV/ROS- stressed human keratinocyte and fibroblast cells. ALTEX. 2019;36(2):231-244. doi: 10.14573/altex.1808201. Epub 2018 Nov 27. PMID: 30488083. 3: Diffey B. New Sunscreens and the Precautionary Principle. JAMA Dermatol. 2016 May 1;152(5):511-2. doi: 10.1001/jamadermatol.2015.6069. PMID: 26885870. 4: L'alloret F, Candau D, Seité S, Pygmalion MJ, Ruiz L, Josso M, Meaudre H, Gauchet L, Pena AM, Colonna A. New combination of ultraviolet absorbers in an oily emollient increases sunscreen efficacy and photostability. Dermatol Ther (Heidelb). 2012 Dec;2(1):4. doi: 10.1007/s13555-012-0004-8. Epub 2012 Apr 17. PMID: 23205327; PMCID: PMC3510392. 5: Kim D, Kim S, Kim SA, Choi M, Kwon KJ, Kim M, Kim DS, Kim SH, Choi BK. Simultaneous analysis and monitoring of 16 UV filters in cosmetics by high- performance liquid chromatography. J Cosmet Sci. 2012 Mar-Apr;63(2):103-17. PMID: 22591562. 6: Shaw T, Simpson B, Wilson B, Oostman H, Rainey D, Storrs F. True photoallergy to sunscreens is rare despite popular belief. Dermatitis. 2010 Jul- Aug;21(4):185-98. PMID: 20646669. 7: DeLeo VA, Clark S, Fowler J, Poncet M, Loesche C, Soto P. A new ecamsule- containing SPF 40 sunscreen cream for the prevention of polymorphous light eruption: a double-blind, randomized, controlled study in maximized outdoor conditions. Cutis. 2009 Feb;83(2):95-103. PMID: 19326695. 8: Fourtanier A, Moyal D, Seité S. Sunscreens containing the broad-spectrum UVA absorber, Mexoryl SX, prevent the cutaneous detrimental effects of UV exposure: a review of clinical study results. Photodermatol Photoimmunol Photomed. 2008 Aug;24(4):164-74. doi: 10.1111/j.1600-0781.2008.00365.x. PMID: 18717957. 9: Forestier S. Rationale for sunscreen development. J Am Acad Dermatol. 2008 May;58(5 Suppl 2):S133-8. doi: 10.1016/j.jaad.2007.05.047. PMID: 18410799. 10: León Z, Balaguer A, Chisvert A, Salvador A, Herráez M, Díez O. A reversed- phase ion-interaction chromatographic method for in-vitro estimation of the percutaneous absorption of water-soluble UV filters. Anal Bioanal Chem. 2008 Jun;391(3):859-66. doi: 10.1007/s00216-008-2013-0. Epub 2008 Mar 27. PMID: 18365182. 11: Grégoire S, Patouillet C, Noé C, Fossa I, Benech Kieffer F, Ribaud C. Improvement of the experimental setup for skin absorption screening studies with reconstructed skin EPISKIN. Skin Pharmacol Physiol. 2008;21(2):89-97. doi: 10.1159/000112959. Epub 2008 Jan 11. PMID: 18187968. 12: Tomecki MH. OTC product: Anthelios SX. J Am Pharm Assoc (2003). 2007 Sep- Oct;47(5):672. doi: 10.1331/JAPhA.2007.07527. PMID: 17848358. 13: D'Souza G, Evans GR; Plastic Surgery Educational Foundation Technology Assessment Committee. Mexoryl: a review of an ultraviolet a filter. Plast Reconstr Surg. 2007 Sep 15;120(4):1071-5. doi: 10.1097/01.prs.0000280561.02915.3a. PMID: 17805138. 14: A new sunscreen agent. Med Lett Drugs Ther. 2007 May 21;49(1261):41-3. Erratum in: Med Lett Drugs Ther. 2007 Oct 8;49(1271):84. PMID: 17505409. 15: I've heard there's a new sunscreen that's supposed to offer better skin protection. Can you tell me more? Mayo Clin Womens Healthsource. 2007 Jun;11(6):8. PMID: 17476186. 16: The FDA approves new over-the-counter sunscreen. FDA Consum. 2006 Sep- Oct;40(5):4. PMID: 17326301. 17: Moyal D. Prevention of ultraviolet-induced skin pigmentation. Photodermatol Photoimmunol Photomed. 2004 Oct;20(5):243-7. doi: 10.1111/j.1600-0781.2004.00111.x. PMID: 15379874. 18: Benech-Kieffer F, Meuling WJ, Leclerc C, Roza L, Leclaire J, Nohynek G. Percutaneous absorption of Mexoryl SX in human volunteers: comparison with in vitro data. Skin Pharmacol Appl Skin Physiol. 2003 Nov-Dec;16(6):343-55. doi: 10.1159/000072929. PMID: 14528058. 19: Chisvert A, Salvador A. Determination of water-soluble UV-filters in sunscreen sprays by liquid chromatography. J Chromatogr A. 2002 Nov 22;977(2):277-80. doi: 10.1016/s0021-9673(02)01411-5. PMID: 12456118. 20: Moyal D, Chardon A, Kollias N. UVA protection efficacy of sunscreens can be determined by the persistent pigment darkening (PPD) method. (Part 2). Photodermatol Photoimmunol Photomed. 2000 Dec;16(6):250-5. doi: 10.1034/j.1600-0781.2000.160603.x. PMID: 11132127.