A natural apocarotenoid with diverse biological activities
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Transcrocetin

Item No. 24217

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,6,11,15-tetramethyl-2E,4E,6E,8E,10E,12E,14E-hexadecaheptaenedioic acid
CAS Number
27876-94-4
Synonyms
  • NSC 407300
Molecular Formula
C20H24O4
Formula Weight
328.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 2 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 0.1 mg/ml
λmax
426, 451 nm
SMILES
OC(/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C(O)=O)=O
InChi Code
InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+
InChi Key
PANKHBYNKQNAHN-MQQNZMFNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $90

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    10 mg

    $168

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    25 mg

    $288

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    50 mg

    $527

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    Product Description

    Transcrocetin is a natural apocarotenoid isolated from C. sativus and G. jasminoides that has antioxidant, antiproliferative, anti-inflammatory, cardioprotective, and antinociceptive properties.1,2,3,4,5,6 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC50 = 17.8 μg/ml) and inhibits growth of MKN28 stomach, MCF-7 breast, and Caco-2 colon cancer cell lines (IC50s = 53, 63, and 103 μM, respectively).2,3 Transcrocetin (20 μM) protects primary rat microglial cells from LPS-induced death and decreases LPS-induced production of intracellular reactive oxygen species (ROS), TNF-α, IL-1β, and NF-κB.4 Transcrocetin (100 mg/kg) increases the level of glutathione (GSH), catalase (CAT), creatine kinase (CK), and lactate dehydrogenase (LDH) in cardiac tissue in a rat model of myocardial infarction induced by isoproterenol (Item No. 15592).5 It also increases the pressure threshold and latency to withdrawal in response to mechanical and thermal stimuli, respectively, indicating a decrease in allodynia in a mouse model of spared nerve injury when administered intrathecally at a dose of 30 mg/kg.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pfister, S.L., Meyer, P., Steck, A., et al. Isolation and structure elucidation of carotenoid−glycosyl esters in gardenia fruits (Gardenia jasminoides Ellis) and saffron (Crocus sativus Linne). J. Agric. Food Chem. 44(9), 2612-2615 (1996).

    2. Kanakis, C.D., Tarantilis, P.A., Tajmir-Riahi, H.A., et al. Crocetin, dimethylcrocetin, and safranal bind human serum albumin: Stability and antioxidative properties. J. Agric. Food Chem. 55(3), 970-977 (2007).

    3. Oliveira, H., Cai, X., Zhang, Q., et al. Gastrointestinal absorption, antiproliferative and anti-inflammatory effect of the major carotenoids of Gardenia jasminoides Ellis on cancer cells. Food Funct. 8(4), 1672-1679 (2017).

    4. Nam, K.N., Park, Y.-M., Jung, H.-J., et al. Anti-inflammatory effects of crocin and crocetin in rat brain microglial cells. Eur. J. Pharmacol. 648(1-3), 110-116 (2010).

    5. Zhang, W., Li, Y., and Ge, Z. Cardiaprotective effect of crocetin by attenuating apoptosis in isoproterenol induced myocardial infarction rat model. Biomed. Pharmacother. 93, 376-382 (2017).

    6. Wang, X., Zhang, G., Qiao, Y., et al. Crocetin attenuates spared nerve injury-induced neuropathic pain in mice. J. Pharmacol. Sci. 135(4), 141-147 (2017).