An apocarotenoid with diverse biological activities
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Bixin

Item No. 37802

Technical Information
Formal Name
2E,4Z,8,13,17-tetramethyl-2,4,6E,8E,10E,12E,14E,16E,18E-eicosanonaenedioic acid, 1-methyl ester
CAS Number
6983-79-5
Synonyms
  • α-Bixin
  • cis-Bixin
Molecular Formula
C25H30O4
Formula Weight
Purity
≥98%
A solid
DMSO: Soluble: ≥10 mg/ml
SMILES
OC(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)\C=C\C(OC)=O)=O
InChi Code
InChI=1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15-
InChi Key
RAFGELQLHMBRHD-SLEZCNMESA-N
Origin
Plant/Bixa orellana
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Bixin is an apocarotenoid that has been found in B. orellana and has diverse biological activities.1 It is the principal compound in the color additive annatto.2 Bixin inhibits the proliferation of MCF-7 breast, HeLa cervical, and A549 lung cancer cells (IC50s = 14.38, 43.87, and 259.38 µM, respectively). Bixin (10 mg/kg per day) increases glutathione (GSH) levels and reduces mercury-induced DNA damage in rat hepatocytes and leukocytes.3 It induces nuclear factor erythroid 2-related factor 2 (Nrf2) transcriptional activity in a reporter assay and increases levels of GSH and glutamate-cysteine ligase modifier subunit (GCLM).4 It reduces cutaneous photodamage from solar UV exposure in mice in a Nrf2-dependent manner when administered at a dose of 200 mg/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bouvier, F., Dogbo, O., and Camara, B. Biosynthesis of the food and cosmetic plant pigment bixin (annatto). Science 300(5628), 2089-2091 (3003).

    2. Kusmita, L., Franyoto, Y.D., Mutmainah, M., et alBixa orellana L. carotenoids: antiproliferative activity on human lung cancer, breast cancer, and cervical cancer cells in vitro. Natural Product Research 36(24), 6421-6427 (2022).

    3. Barcelos, G.R.M., Grotto, D., Serpeloni, J.M., et alBixin and norbixin protect against DNA-damage and alterations of redox status induced by methylmercury exposure in vivo. Environ. Mol. Mutagen. 53(7), 535-541 (2012).

    4. Tao, S., Park, S.L., de la Vega, M.R., et alSystemic administration of the apocarotenoid bixin protects skin against solar UV-induced damage through activation of NRF2. Free Rad. Biol. Med. 89, 690-700 (2015).