CAS 27975-19-5|Isosteviol

Introduction：Basic information about CAS 27975-19-5|Isosteviol, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Isosteviol BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Synonyms

Common Name	Isosteviol
CAS Number	27975-19-5	Molecular Weight	318.450
Density	1.2±0.1 g/cm3	Boiling Point	455.6±38.0 °C at 760 mmHg
Molecular Formula	C₂₀H₃₀O₃	Melting Point	228.0 to 232.0 °C
MSDS	ChineseUSA	Flash Point	243.5±23.3 °C

Names

Name	Isosteviol
Synonym	More Synonyms

Isosteviol BiologicalActivity

Description	Isosteviol is a derivative of stevioside, a constituent of Stevia rebaudiana, which is commonly used as a noncaloric sugar substitute in Japan and Brazil.Target:Isosteviol dose-dependently relaxed the vasopressin (10-8 M)-induced vasoconstriction in isolated aortic rings with or without endothelium. However, in the presence of potassium chloride (3×10-2 M), the vasodilator effect of isosteviol on arterial strips disappeared. Only the inhibitors specific for the ATP-sensitive potassium (KATP) channel or small conductance calcium-activated potassium (SKCa) channel inhibited the vasodilator effect of isosteviol in isolated aortic rings contracted with 10-8 M vasopressin [1]. The attenuation by isosteviol of the vasopressin- and phenylephrine-induced increase in [Ca (2+)]i was inhibited by glibenclamide, apamin and 4-aminopyridine but not by charybdotoxin. Furthermore, the inhibitory action of isosteviol on [Ca (2+)]i was blocked when A7r5 cells co-treated with glibenclamide and apamin in conjunction with 4-aminopyridine were present [2]. Isosteviol (1-100 micromol/l) inhibits angiotensin-II-induced DNA synthesis and endothelin-1 secretion. Measurements of 2'7'-dichlorofluorescin diacetate, a redox-sensitive fluorescent dye, showed an isosteviol-mediated inhibition of intracellular reactive oxygen species generated by the effects of angiotensin II [3].
Related Catalog	Signaling Pathways >>Others >>OthersResearch Areas >>Cardiovascular DiseaseNatural Products >>Terpenoids and Glycosides
References	[1]. Wong KL, et al. Isosteviol acts on potassium channels to relax isolated aortic strips of Wistar rat. Life Sci. 2004 Mar 26;74(19):2379-87. [2]. Wong KL, et al. Isosteviol as a potassium channel opener to lower intracellular calcium concentrations in cultured aortic smooth muscle cells. Planta Med. 2004 Feb;70(2):108-12. [3]. Wong KL, et al. Antiproliferative effect of isosteviol on angiotensin-II-treated rat aortic smooth muscle cells. Pharmacology. 2006;76(4):163-9.

Description

Isosteviol is a derivative of stevioside, a constituent of Stevia rebaudiana, which is commonly used as a noncaloric sugar substitute in Japan and Brazil.Target:Isosteviol dose-dependently relaxed the vasopressin (10-8 M)-induced vasoconstriction in isolated aortic rings with or without endothelium. However, in the presence of potassium chloride (3×10-2 M), the vasodilator effect of isosteviol on arterial strips disappeared. Only the inhibitors specific for the ATP-sensitive potassium (KATP) channel or small conductance calcium-activated potassium (SKCa) channel inhibited the vasodilator effect of isosteviol in isolated aortic rings contracted with 10-8 M vasopressin [1]. The attenuation by isosteviol of the vasopressin- and phenylephrine-induced increase in [Ca (2+)]i was inhibited by glibenclamide, apamin and 4-aminopyridine but not by charybdotoxin. Furthermore, the inhibitory action of isosteviol on [Ca (2+)]i was blocked when A7r5 cells co-treated with glibenclamide and apamin in conjunction with 4-aminopyridine were present [2]. Isosteviol (1-100 micromol/l) inhibits angiotensin-II-induced DNA synthesis and endothelin-1 secretion. Measurements of 2'7'-dichlorofluorescin diacetate, a redox-sensitive fluorescent dye, showed an isosteviol-mediated inhibition of intracellular reactive oxygen species generated by the effects of angiotensin II [3].

Related Catalog

Signaling Pathways >>Others >>OthersResearch Areas >>Cardiovascular DiseaseNatural Products >>Terpenoids and Glycosides

References

[1]. Wong KL, et al. Isosteviol acts on potassium channels to relax isolated aortic strips of Wistar rat. Life Sci. 2004 Mar 26;74(19):2379-87.

[2]. Wong KL, et al. Isosteviol as a potassium channel opener to lower intracellular calcium concentrations in cultured aortic smooth muscle cells. Planta Med. 2004 Feb;70(2):108-12.

[3]. Wong KL, et al. Antiproliferative effect of isosteviol on angiotensin-II-treated rat aortic smooth muscle cells. Pharmacology. 2006;76(4):163-9.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	455.6±38.0 °C at 760 mmHg
Melting Point	228.0 to 232.0 °C
Molecular Formula	C₂₀H₃₀O₃
Molecular Weight	318.450
Flash Point	243.5±23.3 °C
Exact Mass	318.219482
PSA	54.37000
LogP	4.13
Vapour Pressure	0.0±2.4 mmHg at 25°C
Index of Refraction	1.551
InChIKey	KFVUFODCZDRVSS-XCDUIVLNSA-N
SMILES	CC12CCC3C(CCC4C(C)(C(=O)O)CCCC34C)(CC1=O)C2
Storage condition	-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RC5532500

CHEMICAL NAME :: 17-Norkauran-18-oic acid, 13-methyl-16-oxo-, (4-alpha,8-beta,13-beta)-

CAS REGISTRY NUMBER :: 27975-19-5

LAST UPDATED :: 199703

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C20-H30-O3

MOLECULAR WEIGHT :: 318.50

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3160 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 671 mg/kg

TOXIC EFFECTS :: Vascular - regional or general arteriolar or venous dilation Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 503 mg/kg

TOXIC EFFECTS :: Vascular - regional or general arteriolar or venous dilation Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5060 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1070 mg/kg

TOXIC EFFECTS :: Vascular - regional or general arteriolar or venous dilation Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 612 mg/kg

TOXIC EFFECTS :: Vascular - regional or general arteriolar or venous dilation Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994

Safety Information

RIDADR	NONH for all modes of transport

Synonyms

16-oxo-ent-beyeran-19-oic acid

iso-Steviol

ent-16-oxobeyeran-19-oic acid

16-oxobeyeran-19-oic acid

16-Oxobeyeran-18-oic acid

ent-16-ketobeyeran-19-oic acid

Recommended......