Steviol

Steviol

Names
IUPAC name (5β,8α,9β,10α,13α)-13-Hydroxykaur-16-en-18-oic acid
Other names Hydroxydehydrostevic acid; 13-Hydroxykaurenoic acid; ent-13-Hydroxy-kauran-16-en-19-oic acid
Identifiers
CAS Number	471-80-7 N
ChEMBL	ChEMBL444122 N
ChemSpider	398979 Y
Jmol 3D model	Interactive image
PubChem	452967
UNII	4741LYX6RT Y
InChI InChI=1S/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)/t14-,15-,17+,18+,19+,20-/m0/s1 Y Key: QFVOYBUQQBFCRH-VQSWZGCSSA-N Y InChI=1/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)/t14-,15-,17+,18+,19+,20-/m0/s1 Key: QFVOYBUQQBFCRH-VQSWZGCSBR
SMILES O=C(O)[C@]4([C@H]3CC[C@@]21C[C@](O)(\C(=C)C1)CC[C@H]2[C@]3(C)CCC4)C
Properties
Chemical formula	C20H30O3
Molar mass	318.46 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Steviol is a diterpene first isolated from the plant Stevia rebaudiana in 1931. Its chemical structure was not fully elucidated until 1960.

Steviol occurs in the plant as steviol glycosides, sweet compounds that have found widespread use as sugar substitutes.

Biosynthesis

In Stevia rebaudiana, the biosynthesis of steviol is confined to green tissues. The precursors of steviol are synthesized via the non-mevalonate pathway located in plant cell plastids, which produces isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). IPP and DMAPP are converted to geranylgeranyl diphosphate (GGDP), which is the precursor of many diterpenoids, by GGDP synthase. GPDP is made into a cyclic compound, copalyl diphosphate (CDP), by CDP synthase, after which kaurene is produced by another cyclization catalyzed by kaurene synthase.

The kaurene is then transferred to the endoplasmic reticulum, where it is oxidized to kaurenoic acid by kaurene oxidase in a reaction that uses up oxygen and NADPH. Then steviol is produced by hydroxylation. The steviol is subsequently glycosylated in the cytoplasm.

File:Bio synthesis of steviol glycoside 01.png

Biosynthesis of steviol

External links

• PubChem summary of steviol molecule