Article · Wikipedia archive · Last revised Jun 15, 2026

Scopolin

Scopolin is a glucoside of scopoletin formed by the action of the enzyme scopoletin glucosyltransferase. It occurs in Chamaemelum nobile.

Last revised
Jun 15, 2026
Read time
≈ 1 min
Length
236 w
Citations
5
Source
Wikipedia ↗
Scopolin
source ↗
Names
IUPAC name
7-(β-D-Glucopyranosyloxy)-6-methoxy-2H-1-benzopyran-2-one
Systematic IUPAC name
6-Methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-1-benzopyran-2-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
    Key: SGTCGCCQZOUMJJ-YMILTQATSA-N
  • InChI=1/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
    Key: SGTCGCCQZOUMJJ-YMILTQATBT
  • COC1=C(C=C2C(=C1)C=CC(=O)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
Properties
C16H18O9
Molar mass 354.311 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Scopolin is a glucoside of scopoletin formed by the action of the enzyme scopoletin glucosyltransferase.1 It occurs in Chamaemelum nobile.2

Biosynthesis

Scopoletin glucosyltransferase transfers a glucose unit from UDP-glucose to form scopoletin from scopolin:

2D representation of the chemical structure of scopoletin .
scopoletin
+ UDP-glucose
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of scopolin.
scopolin


The enzyme has been characterised from tobacco and Duboisia myoporoides.134

References

References

  1. Hino F, Okazaki M and Miura Y (1982). "Effect of 2,4-dichlorophenoxyacetic acid on glucosylation of scopoletin to scopolin in tobacco tissue-culture". Plant Physiol. 69 (4): 810–813. doi:10.1104/pp.69.4.810. PMC 426310. PMID 16662301.
  2. Hänsel, Rudolf; Sticher, Otto (2010). Pharmakognosie – Phytopharmazie (in German) (9th ed.). Springer Medizin Verlag. p. 1076. doi:10.1007/978-3-642-00963-1. ISBN 978-3-642-00962-4.
  3. Steck, Warren (1967). "The Biosynthetic Pathway from Caffeic Acid to Scopolin in Tobacco Leaves". Canadian Journal of Biochemistry. 45 (12): 1995–2003. doi:10.1139/o67-233. ISSN 1208-6002. PMID 6082583.
  4. Betry, P.; Fliniaux, M.A.; Mackova, M.; Gillet, F.; Macek, T.; Jacquin-Dubreuil, A. (1995). "Scopoletin-glucosyltransferase Activity from Duboisia myoporoides; Improvement of Cultivation Conditions and Crude Extract Preparation Procedure". Journal of Plant Physiology. 146 (4): 503–507. Bibcode:1995JPPhy.146..503B. doi:10.1016/S0176-1617(11)82015-8. ISSN 0176-1617.