5Beta-Scymnol

5Beta-Scymnol, also known simply as scymnol, is a synthetic INCI-listed skin conditioning ingredient.[1][2][3] The molecule is a steroid derivative that behaves as a hydroxyl radical scavenger and is used for the treatment of skin blemishes such as blocked pores and acne.[4][5]

5Beta-Scymnol
Names
IUPAC name
(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R,5R)-5,7-Dihydroxy-6-(hydroxymethyl)heptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C27H48O6/c1-15(4-7-22(31)16(13-28)14-29)19-5-6-20-25-21(12-24(33)27(19,20)3)26(2)9-8-18(30)10-17(26)11-23(25)32/h15-25,28-33H,4-14H2,1-3H3/t15-,17+,18-,19-,20+,21+,22-,23-,24+,25+,26+,27-/m1/s1
    Key: DIPHJTHZUWDJIK-JPLAUYQNSA-N
  • C[C@H](CC[C@H](C(CO)CO)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
Properties
C27H48O6
Molar mass 468.675 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

History

The molecule was identified and isolated from shark tissues by Professor Takuo Kosuge, Shizuoka College of Pharmacy, Shizuoka, Japan during the 1980s.[4] Based on usage as a traditional folk remedy, it was hypothesised the ingredient may be effective for the treatment of scalds, blemishes and acne.[6][7][8]

Traits

5Beta-Scymnol is a hydroxyl (OH) free radical scavenger.[5] Scymnol's role in quenching free radicals may play a role in inhibiting acne.[8][9]

References
  1. "INCI". Personal Care Products Council.
  2. "SODIUM SCYMNOL SULFATE - Ingrédient INCI Beauty". incibeauty.com. Retrieved 2022-05-30.
  3. Dunlop, K.J.; Barnetson, R.S. (February 1995). "A comparative study of isolutrol versus benzoyl peroxide in the treatment of acne". The Australasian Journal of Dermatology. 36 (1): 13–15. doi:10.1111/j.1440-0960.1995.tb00917.x. ISSN 0004-8380. PMID 7763215. S2CID 23139723.
  4. Chaston, Ian (2017-01-28). Technological Entrepreneurship: Technology-Driven vs Market-Driven Innovation. Springer. ISBN 978-3-319-45850-2.
  5. Macrides et al, A comparison of the hydroxyl radical scavenging properties of the shark bile steroid 5β-scymnol and plant pycnogenols, Biochem Mol Biol Int. 1997 Sep;42(6):1249-60
  6. Kosuge, Y., Kosuge, T., Tsuji, K., Ishida, H., and Broadbent, J. M. (1989). Scymnol sulphate salts isolated from shark tissues for the treatment of liver and skin ailments (Patent: PCTInt Appl. WO 8801274-C.I. CO7J31/ 00). Chem. Abslr. 110, 88640g
  7. Muthusamy, Visalini; Hodges, Lynn D.; Macrides, Theodore A.; Boyle, Glen M.; Piva, Terrence J. (2011). "Effect of Novel Marine Nutraceuticals on IL-1α-Mediated TNF-α Release from UVB-Irradiated Human Melanocyte-Derived Cells". Oxidative Medicine and Cellular Longevity. 2011: 728645. doi:10.1155/2011/728645. ISSN 1942-0900. PMC 3179886. PMID 21961050.
  8. Guardiola-Griffiths, Cristina (2011-09-01). "Medieval mean girls: on sexual rivalry and the uses of cosmetics in La Celestina". EHumanista. 19: 172–193.
  9. Zasloff, M.; Adams, A. P.; Beckerman, B.; Campbell, A.; Han, Z.; Luijten, E.; Meza, I.; Julander, J.; Mishra, A.; Qu, W.; Taylor, J. M.; Weaver, S. C.; Wong, G. C. (2011). "Squalamine as a broad-spectrum systemic antiviral agent with therapeutic potential". Proceedings of the National Academy of Sciences of the United States of America. 108 (38): 15978–15983. Bibcode:2011PNAS..10815978Z. doi:10.1073/pnas.1108558108. PMC 3179074. PMID 21930925.
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