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ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid

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ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid Basic information

Product Name:
ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid
Synonyms:
  • ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid
  • (4alpha,11beta)-11-Hydroxy-15-oxokaur-16-en-18-oic acid
  • Pteris diterpenoid 5F
  • ent-11alpha-Hydroxy-15-oxokaur-16-en-19-oic acid
  • Kaur-16-en-18-oic acid, 11-hydroxy-15-oxo-, (4α,11β)-
  • (1R,4S,5R,9R,10R)-11-Hydroxy-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
CAS:
57719-81-0
MF:
C20H28O4
MW:
332.44
Mol File:
57719-81-0.mol
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ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid Chemical Properties

Boiling point:
516.6±50.0 °C(Predicted)
Density 
1.23±0.1 g/cm3(Predicted)
pka
4.62±0.60(Predicted)
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ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid Usage And Synthesis

Uses

ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid is an anti-melanin synthesis tyrosinase inhibitor, which can be isolated from Pteris fern. ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid regulates the melanogenesis transcription factor microphthalmia-associated transcription factor (MITF). The 11α-OH, 15-oxo and 16-en moieties of ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid are key fragments that inhibit melanin synthesis. The 19-COOH moiety has been implicated in the inhibition of cytotoxicity associated with 11α-OH KA and related compounds[1].

References

[1] Kuroi A, et al. The Importance of 11-OH, 15-oxo, and 16-en Moieties of 11-Hydroxy-15-oxo-kaur-16-en-19-oic Acid in Its Inhibitory Activity on Melanogenesis. Skin Pharmacol Physiol. 2017;30(4):205-215. DOI:10.1159/000475471

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