8810. Stevioside

Nomenclature

CAS number: 57817-89-7
(4α)-13-[(2-O-β-d-Glucopyranosyl-β-d-glucopyranosyl)oxy]kaur-16-en-18-oic acid β-d-glucopyranosyl ester; steviosin.
C38H60O18; mol wt 804.87.
C 56.71%, H 7.51%, O 35.78%.

Description and references

Intensely sweet, steviol glycoside isolated from the leaves of the stevia plant, Stevia rebaudiana Bert., Asteraceae. Structurally similar to the rebaudiosides, q.v. Isoln and characterization: M. Bridel, R. Lavieille, Compt. Rend. 192, 1123 (1931). Structure of glucose moieties: H. B. Wood et al., J. Org. Chem. 20, 875 (1955) DOI. Total synthesis: T. Ogawa et al., Tetrahedron 36, 2641 (1980) DOI. Toxicology study: L. Xili et al., Food Chem. Toxicol. 30, 957 (1992) DOI PubMed. Stability and interaction with food ingredients: G. Th. Kroyer, Lebensm. Wiss. Technol. 32, 509 (1999) DOI. Comparison of extraction methods: J. Pól et al., Anal. Bioanal. Chem. 388, 1847 (2007) DOI PubMed. Review of biosynthesis, metabolism and toxicology: J. M. C. Geuns, Phytochemistry 64, 913-921 (2003) DOI PubMed; of pharmacology and therapeutic applications: V. Chatsudthipong, C. Muanprasat, Pharmacol. Ther. 121, 41-54 (2009) DOI PubMed.

Chemical structure

Properties

Hygroscopic crystals, mp 198°. [α]D25 39.3° (c = 5.7 in H2O). 300 times as sweet as cane sugar. One gram dissolves in 800 ml water. Sol in dioxane. Slightly sol in alc.

Use

Non-nutritive sweetener.