A monoterpene
Related Products
Parent Compound(s)
19997Loganin
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Secologanin

Item No. 20647

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester
CAS Number
19351-63-4
Synonyms
  • NSC 640525
Molecular Formula
C17H24O10
Formula Weight
388.4
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: Slightly soluble
SMILES
OC[C@H]1O[C@@H](O[C@@]2([H])[C@H](C=C)[C@H](CC=O)C(C(OC)=O)=CO2)[C@H](O)[C@@H](O)[C@@H]1O
InChi Code
InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1
InChi Key
CSKKDSFETGLMSB-NRZPKYKESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $44

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    5 mg

    $165

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    Product Description

    Secologanin is a monoterpene that has been found in V. rosea and is an intermediate in the synthesis of monoterpene indole alkaloids from geraniol.1,2 It is a metabolite of loganin (Item No. 19997) formed by the cytochrome P450 (CYP) isoform CYP72A1, also known as secologanin synthase.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Battersby, A.R., Burnett, A.R., and Parsons, P.G. Alkaloid biosynthesis. XIV. Secologanin: Its conversion into ipecoside and its role as biological precursor of the indole alkaloids. J. Chem. Soc. C Organic 8, 1187-1192 (1969).

    2. Miettinen, K., Dong, L., Navrot, N., et al. The seco-iridoid pathway from Catharanthus roseus. Nat. Commun. 5:3606, (2014).

    3. Irmler, S., Schröder, G., St-Pierre, B., et al. Indole alkaloid biosynthesis in Catharanthus roseus: New enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Plant J. 24(6), 797-804 (2000).