Steviol

Steviol
Names
IUPAC name
13-Hydroxy-5β,8α,9β,10α,13α-kaur-16-en-18-oic acid
Systematic IUPAC name
(4R,4aS,6aR,9S,11aR,11bS)-9-Hydroxy-4,11b-dimethyl-8-methylidenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid
Other names
Hydroxydehydrostevic acid
13-Hydroxykaurenoic acid
ent-13-Hydroxykaur-16-en-19-oic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: QFVOYBUQQBFCRH-VQSWZGCSSA-N checkY
  • 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
  • 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
C20H30O3
Molar mass 318.457 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Steviol is a diterpene first isolated from the plant Stevia rebaudiana in 1931.[1] Its chemical structure was not fully elucidated until 1960.[2]

Steviol occurs in the plant as steviol glycosides, sweet compounds that have found widespread use as sugar substitutes.[3] The aglycon is prepared by enzymatic hydrolysis, since upon acid treatment steviol will undergo Wagner-Meerwein rearrangement to the very stable isosteviol.

  1. ^ Cite error: The named reference brid1931 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference dolder1960 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference brandleCJPS98 was invoked but never defined (see the help page).