Scopolin

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

CAS Number

* 531-44-2 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:16065 Y

ChemSpider |

* 388609

PubChem CID

* 439514

UNII |

* 1Y49270PY8 Y

InChI

* 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

SMILES

* 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

Chemical formula

| 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).

Infobox references

Tracking categories (test):

* SizeSet

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

## 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. PMID 16662301.
2. ↑ Hänsel, Rudolf; Sticher, Otto (2010) (in de). Pharmakognosie – Phytopharmazie (9th ed.). Springer Medizin Verlag. pp. 1076. doi:10.1007/978-3-642-00963-1. ISBN 978-3-642-00962-4. https://link.springer.com/book/10.1007/978-3-642-00963-1.

## Bibliography

* Steck, Warren (1967). "Biosynthesis of Scopolin in Tobacco". Canadian Journal of Biochemistry 45 (6): 889–896. doi:10.1139/o67-099. ISSN 1208-6002. PMID 6034703.
* 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.

* v
* t
* e

Types of coumarins

Aglycones|

* Aesculetin
* Ferujol
* Umbelliferone

| O-Methylated|

* Fraxetin
* Herniarin
* Osthol
* Scopoletin

|

glycosides|

* Aesculin
* Fraxin
* Skimmin
* Scopolin
* Umbelliferone 7-apiosylglucoside

derivatives|

| Furanocoumarins|

| Aglycones|

* Angelicin
* Marmesin
* Psoralen
* Vaginol
* Xanthotoxol

| O-Methylated|

* Bergapten
* Isopimpinellin
* Methoxsalen
* Trioxsalen

|

Furanocoumarin glycosides|

* Apterin

Meroterpene furanocoumarin ether|

* Auraptene
* Bergamottin
* Imperatorin

Oligomers|

* Dicoumarol

Synthetic|

* Acenocoumarol
* Coumatetralyl
* Ensaculin
* Ethyl biscoumacetate
* 4-Hydroxycoumarins
* Hymecromone
* Phenprocoumon
* Warfarin

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