Terrein

• CAT Number: R002478
• CAS Number: 582-46-7
• Molecular Formula: C8H10O3
• Molecular Weight: 154.165
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (4S,5R)-4,5-dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
• InChI: InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1
• InChIKey: MHOOPNKRBMHHEC-HZIBQTDNSA-N
• SMILES: CC=CC1=CC(=O)C(C1O)O

Terrein(CAS 582-46-7) is a polar, substituted dihydrocyclopentenone first reported by Raistrick and colleagues in the 1930s and subsequently found in a number of Aspergillus and Penicillium species.
Recent research shows that terrein reduces melanin synthesis by reducing tyrosinase production via ERK activation, followed by MITF down-regulation. Terrein also reduces human keratinocyte proliferation by inhibiting ERK and by decreasing the expression of cyclin B1 and Cdc2 complex.

Reference

1.Studies in the biochemistry of micro-organisms: The metabolic products of Aspergillus terreus Thom. A new mould metabolic product, terrein. Raistrick H. & Smith G. Biochem. J. 1935, 29, 606.

2.Terrein: a new melanogenesis inhibitor and its mechanism. Park S.H. et al. Cell. Mol. Life Sci. 2004, 61, 2878.

3.Terrein inhibits keratinocyte proliferation via ERK inactivation and G2/M cell cycle arrest. Kim D.S. et al. Exp. Dermatol. 2008, 17, 312.