Stevioside

HCID 442089

Basic information

CAS
57817-89-7
Standard SMILES
C=C1C[C@@]23CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(=O)O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]2CC[C@]1(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C3
InChIKey
UEDUENGHJMELGK-HYDKPPNVSA-N
Molecular formula
C38H60O18
Average molar mass
804.9 g/mol
Monoisotopic mass
804.37796506

Names & identifiers

Preferred name
Stevioside
IUPAC
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
English name
Stevioside
Molecular formula
C38H60O18
Molecular weight
804.88

Names & synonyms

SteviosideSteviosin57817-89-70YON5MXJ9PCHEBI:9271INS NO.960DTXSID7021281FEMA NO. 4763INS-960E-960((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) (1R,4S,5R,9S,10R,13S)-13-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-2-yl)oxy-5,9-dimethyl-14-methylidenetetracyclo(11.2.1.01,10.04,9)hexadecane-5-carboxylate(4bS,8aS)-1-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthrene-3,4-dione
Show more names
GLUCOSYL STEVIOL GLYCOSIDESSTEVIA LEAF EXTRACTSteviosidesStevia 95% (froM Stevia rebaudiana) anhydrousStevioside (90%)Stevioside powderStevioside - min 80%
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylateRefChem:51134DTXCID301281260-975-5RebaudinDiterpene glycosideSTEVIBIOSIDE.ALPHA.-G-SWEET

Database identifiers

CAS
57817-89-7
PubChem CID
442089
DTXSID
DTXSID7021281
ChEMBL
CHEMBL444122
ChEBI
CHEBI:9271
UNII
0YON5MXJ9P
EC Number
260-975-5
Nikkaji
J27.441K

Properties

Computed structural properties

XLogP
-1.2
Topological polar surface area
295 Ų
Hydrogen bond donors
11
Hydrogen bond acceptors
18
Rotatable bonds
10
Heavy atoms
56

Experimental & physicochemical properties

Solubility1.25 mg/mL
Melting Point238 - 239 °C
Physical DescriptionSolid
Collision Cross Section269.64 Ų [M+H]+ [CCS Type: TW]

Physicochemical properties

Melting point
198 °C · 198°C
Boiling point
963.3 · 963.3±65.0 °C(Predicted)
alpha
25 · D25 -39.3° (c = 5.7 in H2O)
Density
1.53 · 1.53±0.1 g/cm3(Predicted)
refractive index
-39.3 ° · -39.3 ° (C=6, H2O)
FEMA
4728 · 4728 | GLUCOSYL STEVIOL GLYCOSIDES

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 85.7% (6 of 7) of all reports.

Warning

H315 (14.3%): Causes skin irritation [Warning Skin corrosion/irritation];H317 (14.3%): May cause an allergic skin reaction [Warning Sensitization, Skin];H319 (14.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 7 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 6 of 7 reports by companies.;There is 1 notification provided by 1 of 7 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Chemical: Kaur-16-en-18-oic acid, 13-[(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-, .beta.-D-glucopyranosyl ester, (4.alpha.)-

Kaur-16-en-18-oic acid, 13-(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy-, .beta.-D-glucopyranosyl ester, (4.alpha.)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (14.3%);Skin Sens. 1 (14.3%);Eye Irrit. 2 (14.3%)

Regulatory information

Regulatory Information · 2 items

Chemical: Kaur-16-en-18-oic acid, 13-[(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-, .beta.-D-glucopyranosyl ester, (4.alpha.)-

Kaur-16-en-18-oic acid, 13-(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy-, .beta.-D-glucopyranosyl ester, (4.alpha.)-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

wgk
3
rtecs
NZ8175000
hs_code
29389090
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-24/25

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed)
Cellular LocationsCytoplasm;Extracellular;Membrane

Uses & manufacturing

Use Classification · 2 items

Food Additives -> SWEETENER -> JECFA Functional Classes

Cosmetics -> Masking; Oral care

Applications · 4 items

OccurrenceStevioside is a naturally occurring sweetener (~200 times sweeter than sucrose) extracted from a South American plant, Stevia rebaudiana Bertoni. The dried leaves, the water extract of leaves, and the refined chemical ingredients, eg, and Rebaudioside A (~300 times sweeter than sucrose), can all be used as sweetening agents. These are collectively referred to as stevia. Discovered in Paraguay and Brazil, the plant was identified in the early 1970s as a plant of high economical value and transported to Japan for cultivation, where the commercialization of stevia leaves extract as a natural sweetener became a success. Today Stevia plant is cultivated primarily in China.

HistoryBecause no food additive petition has been presented to the FDA, stevioside and related materials cannot be used in the United States as food ingredients. An import alert against stevia was issued by the FDA in 1991. In 1995, however, the FDA revised this import alert to allow the importation and use of stevia as a dietary supplement, but not as a sweetener or an ingredient for foods. In 2004, JECFA (Joint Expert Committee of Food Additives) issued a preliminary ADI (Allowed Daily Intake) of 2-mg/kg body weight (based on steviol) for stevia extract. This action may impact favorably on worldwide regulatory approval. As consumer’s demand on naturally sweetened products increases, interest in Stevia, and naturally occurring potent sweeteners in general, is expected to grow. A comprehensive review of stevia is available [Kinghorn, 2002].

UsesStevioside is a glycoside from the stevia plant. Stevioside is a natural sweetening agent with sweetness about 250 times that of sugar with negligible effect on blood glucose. Stevioside, much like other steviol glycoside is known for its application in treatment of many diseases like diabetes and high blood pressure. It is also used as a food additive.

UsesStevioside is a natural, calorie-free sweetener obtained from the leaves of the plant stevia rebaudiana bertoni. it is a steviol glycoside in which steviol’s carboxyl and hydroxyl hydrogen atom is replaced with glu- cose; it has two linked glucose molecules at the hydroxyl site. it is the major steviol glycoside found in the stevia plant and is 250–300 times sweeter than sugar. it is heat and ph stable. it has been associ- ated with a bitter and licorice taste. see steviol glycoside.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Stevioside is a diterpene glycoside that is rubusoside in which the hydroxy group at position 2 of the allylic beta-D-glucoside has been converted to the corresponding beta-D-glucoside. It is a natural herbal sweetener that is 250-300 times sweeter than sucrose (though with a bitter aftertaste), extracted from the Stevia rebaudiana plant native to South America. It has a role as a sweetening agent, an antioxidant, an antineoplastic agent, a hypoglycemic agent, an anti-inflammatory agent and a plant metabolite. It is a diterpene glycoside, an ent-kaurane diterpenoid, a beta-D-glucoside, a tetracyclic diterpenoid and a bridged compound. It is functionally related to a steviol and a rubusoside.

Related reactions

2 records

Compound notes

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