A coumarin derivative with anti-inflammatory and chemopreventative activity
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Auraptene

Item No. 14000

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-2H-1-benzopyran-2-one
CAS Number
495-02-3
Synonyms
  • 7-Geranyloxycoumarin
Molecular Formula
C19H22O3
Formula Weight
298.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMF:PBS(pH7.2) (1:2): 0.3 mg/mlDMSO: 12 mg/mlEthanol: 12 mg/ml
λmax
323 nm
SMILES
O=C1C=CC2=C(C=C(OC/C=C(C)/CC/C=C(C)\C)C=C2)O1
InChi Code
InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
InChi Key
RSDDHGSKLOSQFK-RVDMUPIBSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $32

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    10 mg

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    25 mg

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    50 mg

    $134

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    Cayman Chemical
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    Product Description

    Auraptene is a coumarin derived from citrus plants that bears a geranyloxyl moiety at its C-7. It has anti-inflammatory, anti-carcinogenic, anti-bacterial, neuroprotective, and hepatoprotective activities.1,2,3,4,5 It inhibits leukocyte activation and induces phase II enzymes during the initiation phase of carcinogenesis.1 When examined for its potential use in Alzheimer’s disease treatment, auraptene was shown to inhibit β-secretase (BACE1) activity with an IC50 value of 345.1 μM.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Murakami, A., Nakamura, Y., Tanaka, T., et al. Suppression by citrus auraptene of phorbol ester- and endotoxin-induced inflammatory responses: Role of attenuation of leukocyte activation. Carcinogenesis 21(10), 1843-1850 (2000).

    2. Krishnan, P., Yan, K.J., Windler, D., et al. Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats. BMC Cancer 9, (2009).

    3. Takeda, K., Utsunomiya, H., Kakiuchi, S., et al. Citrus auraptene reduces Helicobacter pylori colonization of glandular stomach lesions in Mongolian gerbils. J. Oleo Sci. 56(5), 253-260 (2007).

    4. Furukawa, Y., Watanabe, S., Okuyama, S., et al. Neurotrophic effect of Citrus auraptene: Neuritogenic activity in PC12 cells. Int. J. Mol. Sci. 13, 5338-5347 (2012).

    5. Sahebkar, A. Citrus auraptene: A potential multifunctional therapeutic agent for nonalcoholic fatty liver disease. Ann. Hepatol. 10(4), 575-577 (2011).

    6. Marumoto, S., and Miyazawa, M. Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor. Bioorg. Med. Chem. 20(2), 784-788 (2012).