REBAUDIOSIDE C

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C44H70O22
Molecular Weight	951.0134
Optical Activity	UNSPECIFIED
Defined Stereocenters	26 / 26
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@]3(C[C@]1(CC3=C)CC[C@]4([H])[C@@](C)(CCC[C@@]24C)C(=O)O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O

InChI

InChIKey=QSRAJVGDWKFOGU-WBXIDTKBSA-N

InChI=1S/C44H70O22/c1-17-12-43-10-6-22-41(3,8-5-9-42(22,4)40(58)65-38-33(57)30(54)26(50)20(14-46)61-38)23(43)7-11-44(17,16-43)66-39-35(64-36-31(55)28(52)24(48)18(2)59-36)34(27(51)21(15-47)62-39)63-37-32(56)29(53)25(49)19(13-45)60-37/h18-39,45-57H,1,5-16H2,2-4H3/t18-,19+,20+,21+,22-,23-,24-,25+,26+,27+,28+,29-,30-,31+,32+,33+,34-,35+,36-,37-,38-,39-,41+,42+,43+,44-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C44H70O22
Molecular Weight	951.0134
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	26 / 26
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27784241
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23203115 | https://www.ncbi.nlm.nih.gov/pubmed/28228527 | https://www.ncbi.nlm.nih.gov/pubmed/24783855 | https://www.ncbi.nlm.nih.gov/pubmed/12419967

Rebaudioside C is a natural primary glycoside constituent of the plant Stevia rebaudiana Bertoni and used as natural non-caloric sweeteners to diabetics and others on carbohydrate-controlled diets. Found in the by-product of Rebaudioside A production, Rebaudioside C is produced through advanced glycoside isolation and specialized extraction processing. While not a sweetener itself, Rebaudioside C has been trialed with nutritive sweeteners and shown to enable a 20-25% reduction in calories. In preclinical studies Rebaudioside C shows potent anti-inflammatory activity in against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. Steviol glycosides have not yet been approved as a sweetener in the European Union, but purified rebaudioside A gained GRAS (Generally Recognized as Safe) status in the USA in 2008, and in the same year the Joint FAO/WHO Expert Committee on Food Additives suggested a temporary admissible daily intake (ADI) of 0–4 mg/kg body weight, expressed as steviol.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
sweet taste receptor complex 1 Target ID: GO:1903767 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21337478	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12419967	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Catalytic hydrogenation of the sweet principles of Stevia rebaudiana, Rebaudioside B, Rebaudioside C, and Rebaudioside D and sensory evaluation of their reduced derivatives.	2012 Nov 16	23203115

Patents

Sample Use Guides

In Vivo Use Guide

Mice were treated with Rebaudioside C (200mg/ear

Route of Administration: Topical

In Vitro Use Guide

The PC12 cells were used for activity evaluation. Cell viability was measured by trypan blue exclusion assay. The PC12 cells were incubated in DMEM containing serum with 0 to 10,000 ng/mL stevioside for 72 h. After the incubation, cells were stained in 0.25% trypan blue solution in phosphate-buffered saline. Total cells and trypan blue-stained cells were counted using a hemocytometer. Cell viability was expressed as a percentage against the total cell number in each experiment.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:23:55 UTC 2023` Edited by `admin` on `Sat Dec 16 08:23:55 UTC 2023`
Record UNII	FE0M8Z5L2E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

REBAUDIOSIDE C

Common Name

English

KAUR-16-EN-18-OIC ACID, 13-((O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->3))-.BETA.-D-GLUCOPYRANOSYL)OXY)-, .BETA.-D-GLUCOPYRANOSYL ESTER, (4.ALPHA.)-

Systematic Name

English

(-)-REBAUDIOSIDE C

Common Name

English

REBAUDIOSIDE C, (-)-

Common Name

English

FEMA NO. 4720

Code

English

REBC

Common Name

English

REBAUDIOSIDE C [MI]

Common Name

English

DULCOSIDE B

Common Name

English

Code System Code Type Description

PUBCHEM

60208888