# Steviol

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Steviol
> Markdown URL: https://mediated.wiki/source/Steviol.md
> Source: https://en.wikipedia.org/wiki/Steviol
> Source revision: 1300696843
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470470860
| ImageFile = steviol structure.svg
| ImageSize = 200px
| ImageFile1     = Steviol-3D ball-and-stick.png
| ImageSize1     = 
| IUPACName = 13-Hydroxy-5β,8α,9β,10α,13α-kaur-16-en-18-oic acid
| SystematicName = (4''R'',4a''S'',6a''R'',9''S'',11a''R'',11b''S'')-9-Hydroxy-4,11b-dimethyl-8-methylidenetetradecahydro-6a,9-methanocyclohepta[''a'']naphthalene-4-carboxylic acid
| OtherNames = Hydroxydehydrostevic acid<br>13-Hydroxykaurenoic acid<br>''ent''-13-Hydroxykaur-16-en-19-oic acid
|Section1={{Chembox Identifiers
| CASNo = 471-80-7
| CASNo_Ref = {{cascite|changed|??}}
| PubChem = 452967
| ChemSpiderID = 398979
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI = 145024
| ChEMBL = 444122      
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4741LYX6RT
| 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
| 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
| InChIKey = QFVOYBUQQBFCRH-VQSWZGCSBR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QFVOYBUQQBFCRH-VQSWZGCSSA-N
  }}
|Section2={{Chembox Properties
| C=20 | H=30 | O=3
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility =
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt =
  }}
}}

'''Steviol''' is a [diterpene](/source/diterpene) first isolated from the plant ''[Stevia rebaudiana](/source/Stevia_rebaudiana)'' in 1931.<ref name=brid1931/>  Its chemical structure was not fully elucidated until 1960.<ref name=dolder1960/>

Steviol occurs in the plant as [steviol glycoside](/source/steviol_glycoside)s, sweet compounds that have found widespread use as [sugar substitute](/source/sugar_substitute)s.<ref name=brandleCJPS98/> The [aglycon](/source/aglycon) is prepared by enzymatic hydrolysis, since upon acid treatment steviol will undergo [Wagner-Meerwein rearrangement](/source/Wagner-Meerwein_rearrangement) to the very stable isosteviol.

==Biosynthesis==
In ''Stevia rebaudiana'', the [biosynthesis](/source/biosynthesis) of steviol is confined to green tissues.  The precursors of steviol are synthesized via the [non-mevalonate pathway](/source/non-mevalonate_pathway) located in plant cell [plastids](/source/plastids), which produces [isopentenyl pyrophosphate](/source/isopentenyl_pyrophosphate) (IPP) and [dimethylallyl pyrophosphate](/source/dimethylallyl_pyrophosphate) (DMAPP). IPP and DMAPP are converted to [geranylgeranyl diphosphate](/source/geranylgeranyl_diphosphate) (GGDP), which is the precursor of many [diterpenoids](/source/terpenoid), by [GGDP synthase](/source/farnesyltranstransferase).  GPDP is made into a [cyclic compound](/source/cyclic_compound), [copalyl diphosphate](/source/copalyl_diphosphate) (CDP), by [CDP synthase](/source/copalyl_diphosphate_synthase), after which [kaurene](/source/kaurene) is produced by another cyclization catalyzed by [kaurene synthase](/source/ent-kaurene_synthase).

The kaurene is then transferred to the [endoplasmic reticulum](/source/endoplasmic_reticulum), where it is oxidized to [kaurenoic acid](/source/kaurenoic_acid) by [kaurene oxidase](/source/ent-kaurenoic_acid_oxidase) in a reaction that uses up oxygen and [NADPH](/source/NADPH).   Then steviol is produced by hydroxylation. The steviol is subsequently [glycosylated](/source/glycosylation) in the cytoplasm.<ref name=brandle2007/>
{{clear left}}thumb|600px|center|Biosynthesis of steviol<ref name=brandle2007/>{{clear}}

==References==
<references>

<ref name=brandleCJPS98>{{cite journal | author = Brandle J. E., Starratt A. N., Gijzen M. | year = 1998 | title = Stevia rebaudiana: Its agricultural, biological, and chemical properties | journal = Canadian Journal of Plant Science | volume = 78 | issue = 4| pages = 527–536 | doi = 10.4141/P97-114 | doi-access = free }}</ref>

<ref name=brid1931>{{cite journal |author1=Bridel, M. |author2=Lavieille, R. | title = The sweet principle in Kaa-he-e (Stevia rebaudiana. Bertoni). II. Hydrolysis of stevioside by enzymes. III. Steviol by enzymic hydrolysis and isosteviol by acid hydrolysis.    | journal = Bulletin de la Société de Chimie Biologique | year = 1931 | pages = 781–796 | volume = 13}}</ref>

<ref name=brandle2007>{{cite journal | author = Brandle JE, Telmer PG | date = Jul 2007 | title = Steviol glycoside biosynthesis | journal = Phytochemistry | volume = 68 | issue = 14| pages = 1855–63 | pmid = 17397883 | doi = 10.1016/j.phytochem.2007.02.010 | bibcode = 2007PChem..68.1855B }}</ref>

<ref name=dolder1960>{{cite journal |author1=Dolder, Fred |author2=Lichti, Heinz |author3=Mosettig, Erich |author4=Quitt, Peter | title = The structure and stereochemistry of steviol and isosteviol | journal = Journal of the American Chemical Society | year = 1960 | volume = 82  | pages = 246–247 | doi = 10.1021/ja01486a054}}</ref>
</references>

==External links==
* [https://pubchem.ncbi.nlm.nih.gov/substance/598381 PubChem summary of steviol molecule]

Category:Diterpenes
Category:Cyclopentanes
Category:Vinylidene compounds

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Adapted from the Wikipedia article [Steviol](https://en.wikipedia.org/wiki/Steviol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Steviol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.