A benzoquinone with diverse biological activities
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Primin

Item No. 35441

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methoxy-6-pentyl-2,5-cyclohexadiene-1,4-dione
CAS Number
15121-94-5
Molecular Formula
C12H16O3
Formula Weight
Purity
≥98%
A solid
Acetonitrile: solubleEthanol: solubleEthyl Acetate: solubleMethanol: soluble
λmax
267 nm
SMILES
O=C1C=C(C(C(CCCCC)=C1)=O)OC
InChi Code
InChI=1S/C12H16O3/c1-3-4-5-6-9-7-10(13)8-11(15-2)12(9)14/h7-8H,3-6H2,1-2H3
InChi Key
WLWIMKWZMGJRBS-UHFFFAOYSA-N
Origin
Plant/Vaccinium spp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Primin is a benzoquinone that has been found in P. obconica and has diverse biological activities.1,2,3,4 It selectively inhibits COX-2 over COX-1 (IC50s = 0.09 and 5.14 µM, respectively) and induces the production of adrenochrome from epinephrine, a marker of pro-oxidant activity, in a cell-free assay when used at a concentration of 8.81 µM.1 Primin is active against T. brucei rhodesiense and L. donovani (IC50s = 0.144 and 0.711 µM, respectively), as well as S. aureus (IC50 = 8.94 µM).2,3 In vivo, primin induces contact sensitization in guinea pigs.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Landa, P., Kutil, Z., Temml, V., et alRedox and non-redox mechanism of in vitro cyclooxygenase inhibition by natural quinones. Planta Med. 78(4), 326-333 (2011).

    2. Tasdemir, D., Brun, R., Yardley, V., et alAntituberculotic and antiprotozoal activities of primin, a natural benzoquinone: In vitro and in vivo studies. Chem. Biodivers. 3(11), 1230-1237 (2006).

    3. Viegas, F.P.D., Espuri, P.F., Oliver, J.C., et alLeishmanicidal and antimicrobial activity of primin and primin-containing extracts from Miconia willdenowii. Fitoterapia 138, 104297 (2019).

    4. Schulz, K.H., Garbe, I., Hausen, B.M., et alThe sensitizing capacity of naturally occurring quinones. Experimental studies in guinea pigs. II. Benzoquinones. Arch. Dermatol. Res. 264(3), 275-286 (1979).