A secoiridoid glycoside with diverse biological activities
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Secoxyloganin

Item No. 30267

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetic acid
CAS Number
58822-47-2
Molecular Formula
C17H24O11
Formula Weight
404.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5mg/mLDMSO: 5mg/mLEthanol: 10mg/mLPBS (pH 7.2): 10mg/mL
λmax
232 nm
SMILES
OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](C=C)[C@H](CC(O)=O)C(C(OC)=O)=CO2)O1
InChi Code
InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16+,17+/m1/s1
InChi Key
MQLSOVRLZHTATK-PEYNGXJCSA-N
Origin
Plant/Lonicerae flos
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Secoxyloganin is a secoiridoid glycoside that has been found in L. japonica and has diverse biological activities.1,2,3 It is active against E. coli and S. aureus in a disc assay when used at a concentration of 2 mg/disc.1 Secoxyloganin is cytotoxic to human dermal fibroblasts (IC50 = 78.1 µM).2 In vivo, secoxyloganin (10 mg/ml) prevents hen egg white lysozyme-induced decreases in tail vein blood flow, a marker of allergic inflammation, in hen egg white lysozyme-sensitized mice.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Xiong, J., Li, S., Wang, W., et al. Screening and identification of the antibacterial bioactive compounds from Lonicera japonica Thunb. leaves. Food Chem. 138(1), 327-333 (2013).

    2. Zebiri, I., Haddad, M., Duca, L., et al. Biological activities of triterpenoids from Poraqueiba sericea stems. Nat. Prod. Res. 31(11), 1333-1338 (2017).

    3. Oku, H., Ogawa, Y., Iwaoka, E., et al. Allergy-preventive effects of chlorogenic acid and iridoid derivatives from flower buds of Lonicera japonica. Biol. Pharm. Bull. 34(8), 1330-1333 (2011).