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Bridel, M.; Lavieille, R. (1931). "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".
422:
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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
318:
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
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Dolder, Fred; Lichti, Heinz; Mosettig, Erich; Quitt, Peter (1960). "The structure and stereochemistry of steviol and isosteviol".
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84:)-9-Hydroxy-4,11b-dimethyl-8-methylidenetetradecahydro-6a,9-methanocycloheptanaphthalene-4-carboxylic acid
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of steviol is confined to green tissues. The precursors of steviol are synthesized via the
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is prepared by enzymatic hydrolysis, since upon acid treatment steviol will undergo
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556:. Then steviol is produced by hydroxylation. The steviol is subsequently
633:"Stevia rebaudiana: Its agricultural, biological, and chemical properties"
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in 1931. Its chemical structure was not fully elucidated until 1960.
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Brandle JE, Telmer PG (Jul 2007). "Steviol glycoside biosynthesis".
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Except where otherwise noted, data are given for materials in their
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461:, sweet compounds that have found widespread use as
49:13-Hydroxy-5β,8α,9β,10α,13α-kaur-16-en-18-oic acid
631:Brandle J. E., Starratt A. N., Gijzen M. (1998).
533:is produced by another cyclization catalyzed by
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663:: CS1 maint: multiple names: authors list (
587:Bulletin de la Société de Chimie Biologique
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606:Journal of the American Chemical Society
505:(DMAPP). IPP and DMAPP are converted to
342:O=C(O)4(3CC21C(O)(\C(=C)C1)CC23(C)CCC4)C
576:
540:The kaurene is then transferred to the
509:(GGDP), which is the precursor of many
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552:in a reaction that uses up oxygen and
311:Key: QFVOYBUQQBFCRH-VQSWZGCSSA-N
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727:PubChem summary of steviol molecule
321:Key: QFVOYBUQQBFCRH-VQSWZGCSBR
221:
14:
637:Canadian Journal of Plant Science
100:-13-Hydroxykaur-16-en-19-oic acid
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369:
31:
22:
703:10.1016/j.phytochem.2007.02.010
473:to the very stable isosteviol.
457:Steviol occurs in the plant as
403:(at 25 °C , 100 kPa).
448:first isolated from the plant
375:
363:
1:
471:Wagner-Meerwein rearrangement
503:dimethylallyl pyrophosphate
768:
544:, where it is oxidized to
507:geranylgeranyl diphosphate
499:isopentenyl pyrophosphate
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93:Hydroxydehydrostevic acid
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95:13-Hydroxykaurenoic acid
567:Biosynthesis of steviol
517:. GPDP is made into a
568:
493:located in plant cell
491:non-mevalonate pathway
566:
542:endoplasmic reticulum
56:Systematic IUPAC name
752:Vinylidene compounds
695:2007PChem..68.1855B
618:10.1021/ja01486a054
523:copalyl diphosphate
393: g·mol
18:
569:
560:in the cytoplasm.
459:steviol glycosides
430:Infobox references
16:
497:, which produces
483:Stevia rebaudiana
463:sugar substitutes
451:Stevia rebaudiana
438:Chemical compound
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264:CompTox Dashboard
147:Interactive image
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535:kaurene synthase
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358:Chemical formula
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689:(14): 1855–63.
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550:kaurene oxidase
519:cyclic compound
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683:Phytochemistry
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643:(4): 527–536.
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546:kaurenoic acid
529:, after which
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659:cite journal
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558:glycosylated
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527:CDP synthase
511:diterpenoids
487:biosynthesis
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477:Biosynthesis
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187:ChEMBL444122
167:CHEBI:145024
106:Identifiers
97:
91:Other names
81:
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65:
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612:: 246–247.
351:Properties
742:Diterpenes
736:Categories
593:: 781–796.
572:References
525:(CDP), by
501:(IPP) and
386:Molar mass
252:4741LYX6RT
198:ChemSpider
134:3D model (
113:CAS Number
46:IUPAC name
446:diterpene
711:17397883
495:plastids
123:471-80-7
17:Steviol
691:Bibcode
531:kaurene
467:aglycon
442:Steviol
423:what is
421: (
391:318.457
219:PubChem
709:
485:, the
465:. The
418:verify
415:
335:SMILES
232:452967
207:398979
178:ChEMBL
40:Names
554:NADPH
513:, by
444:is a
300:InChI
158:ChEBI
136:JSmol
707:PMID
665:link
243:UNII
80:,11b
76:,11a
699:doi
645:doi
614:doi
548:by
481:In
269:EPA
222:CID
98:ent
68:,6a
64:,4a
738::
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687:68
685:.
673:^
661:}}
657:{{
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60:(4
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413:N
379:3
376:O
370:H
364:C
271:)
267:(
138:)
82:S
78:R
74:S
70:R
66:S
62:R
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