A fungal metabolite with diverse biological activities
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Terrein

Item No. 23496

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4S,5R-dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one
CAS Number
582-46-7
Synonyms
  • NSC 291308
Molecular Formula
C8H10O3
Formula Weight
154.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Soluble
SMILES
O=C1[C@H](O)[C@@H](O)C(/C=C/C)=C1
InChi Code
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
InChi Key
MHOOPNKRBMHHEC-HZIBQTDNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $134

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    5 mg

    $466

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    10 mg

    $729

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    Product Description

    Terrein is a fungal metabolite produced by A. terreus with diverse biological activities.1 It reduces melanin production in Mel-Ab mouse melanocytes in a dose-dependent manner via ERK activation and downregulation of microphthalmia-associated transcription factor (MITF).2 Terrein inhibits proliferation of human keratinocytes and thins the epidermis in a skin equivalent model of psoriasis vulgaris.3 It is antimicrobial, inhibiting the growth of S. aureus, A. hydrophila, E. faecalis, A. flavus, A. alternata, B. sorokiniana, and P. drechsleri (MICs = 1-40 μg/ml).4 Terrein also inhibits growth of A549 lung cancer cells in a dose-dependent manner.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Raistrick, H., and Smith, G. Studies in the biochemistry of micro-organisms. The metabolic products of Aspergillus terreus Thom. A new mould metabolic product—terrein. Biochem J. 29(3), 606-611 (1935).

    2. Park, S.H., Kim, D.S., Kim, W.G., et al. Terrein: A new melanogenesis inhibitor and its mechanism. Cell Mol. Life Sci. 61(22), 2878-2885 (2004).

    3. Kim, D.S., Cho, H.J., Lee, H.K., et al. Terrein, a fungal metabolite, inhibits the epidermal proliferation of skin equivalents. J. Dermatol. Sci. 46(1), 65-68 (2007).

    4. Goutam, J., Sharma, G., Tiwari, V.K., et al. Isolation and characterization of "terrein" an antimicrobial and antitumor compound from endophytic fungus Aspergillus terreus (JAS-2) associated from Achyranthus aspera Varanasi, India. Front. Microbiol. 8, 1334 (2017).