(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Names and Identifiers

Name	(5R-trans)-6-(β-D-glucopyranosyloxy)-5,6-dihydro-5-vinyl-1H,3H-pyrano[3,4-c]pyran-1-one
Synonyms	20831-76-9 GENTIOPICRIN gentiopicroside glucopyranosyloxy)-5,6-dihydro-,(5R-trans)- 1H,3H-Pyrano[3,4-c]pyran-1-one,5-ethenyl-6-(β-D- (5S,6R)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl hexopyranoside (5R)-5β-Vinyl-6α-(β-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one (5R,6S)-1-Oxo-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyr-6-yl-beta-D-glucopyranoside (5R)-5β-Ethenyl-6α-(β-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one (5R,6S)-1-Oxo-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside (5R-trans)-6-(β-D-glucopyranosyloxy)-5,6-dihydro-5-vinyl-1H,3H-pyrano[3,4-c]pyran-1-one (5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside (5R-trans)-5-Ethenyl-6-(b-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(b-D-glucopyranosyloxy)-5,6-dihydro-, (5R,6S)- 1H,3H-pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R,6S)- 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(b-D-glucopyranosyloxy)-5,6-dihydro-, (5R-trans)- (5R-trans)-5-Ethenyl-6-(.beta.-d-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one (5R,6S)-5-ethenyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6-dihydro-3H-pyrano[5,4-c]pyran-1-one (5R,6S)-6-{[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-on (5R,6S)-6-{[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one (5R,6S)-5-éthènyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one
CAS	20831-76-9
EINECS	244-070-2
InChI	InChI=1/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10?,11?,12?,13?,15+,16?/m0/s1

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Physico-chemical Properties

Molecular Formula	C16H20O9
Molar Mass	356.33
Density	1.52±0.1 g/cm3(Predicted)
Melting Point	191°C
Boling Point	667.8±55.0 °C(Predicted)
Specific Rotation(α)	-200 º (c=2, H2O)
Flash Point	247.129°C
Solubility	Soluble in water, methanol, ethanol and other solvents, difficult to tolerate petroleum ether.
Vapor Presure	0mmHg at 25°C
Appearance	White needle crystal
Color	Pale Beige
pKa	12.79±0.70(Predicted)
Storage Condition	2-8°C(protect from light)
Stability	Hygroscopic
Sensitive	Easily absorbing moisture
Refractive Index	1.623
MDL	MFCD00075700
Physical and Chemical Properties	White crystalline powder, soluble in methanol, almost insoluble in ether, derived from Gentiana macrophylla (Tibet, Gansu) Gentiana Gentiana Gentiana, gentian.
In vitro study	Gentiopicroside inhibits P450 activity, with an IC 50 and a K i of 61 µM and 8.12 µM for CYP2A6, also slightly inhibits CYP2E1 activity with an IC 50 of 1.6 mM, but shows no inhibition on CYP1A2 and CYP3A4. Gentiopicroside (12.5, 25 and 50 μM) inhibits RANKL-induced osteoclast formation from mouse bone marrow macrophages (BMMs) in a dose-dependent manner, blocks the expression of osteoclast-related proteins, prevents receptor activator of nuclear factor-κB ligand (RANKL)-triggered JNK and NF-κB activation. Gentiopicroside (50 μM) also inhibits RANKL-induced bone resorption.
In vivo study	Gentiopicroside (20, 40, and 80 mg/kg, p.o.) significantly reduces gastric ulcerindex in mice. Gentiopicroside (20, 40, and 80 mg/kg) also ovbiously decreases the levels of HSP-70, TNF-α, IL-6, MDA and increases ncreased GSH level and SOD activity. In addition, Gentiopicroside normalizes EGF and VEGF level in mice.

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Risk and Safety

HS Code

29389090

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Reference

Reference

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2. Gao Yan, Hao Baocheng, Wu Jincuom, Gesang Zhuoga, Ban Dan, Si Lang Yuzhen, Xing Xiaoyong, Liang Yun, Yang Zhiwei, Wang Lanfang, Hu Yonghao, Liang Jianping, rabatzidan. In vitro and in vivo antibacterial activity of the water decoction of Dankolanpu against Pasteurella multocida [J]. Advances in Animal Medicine, 2019,40(07):43-48.
3. Han Duo, Zhao Zhilian, Liu Weihong, Li Yuehua, Li Haifeng. Quality Evaluation and Quality Equivalence of Three White Medicinal Plants of Gentiana [J]. Northern Horticultural 2016(18):165-170.
4. Yang Wenning, Han Xing, Yang Haiyang, et al. Study on Selection of Quality Control Components of Gentiana Gentiana Gentiana Based on Multi-component Drug Metabolism [J]. World Traditional Chinese Medicine 20202015 Volume 13, 1897-1902,1907 pages, ISTIC, 2020.
5. Wu Xinyi, Liu Xiuzhang, Qu Yunhui, et al. Box-Behnken Design-Response Surface Methodology to Optimize Primary Processing Technology of Gentiana Yunnan [J]. China Pharmacy 20202031 Volume 15 Page 1830-1835 ISTIC PKU CA 2020.
6. Han Duo, Zhao Zhilian, Liu Weihong, et al. Accumulation of Main Effective Components in Leaves of Three Gentiana Medicinal Plants [J]. China Journal of Pharmaceutical Industry 2016 47(007):865-869.
7. Yang Jianhua, Zhu Dandan, Jiang Xiangying, et al. Simultaneous Determination of Five Active Components in Xinjiang Pseudogentian by RP-HPLC Method [J]. 2015 of New Chinese Medicine and Clinical Pharmacology v.26;No.135(06):116-119.
8. Wang Linlin, Yin Haibo, Zhang Ziyan, et al. Correlation Analysis of Different Soil Nitrogen Application Rates and Active Components of Gentiana [J]. Journal of Liaoning University of Traditional Chinese Medicine 2017 019(005):72-75.
9. Han Duo, Zhao Zhilian, Liu Weihong, et al. Study on Main Secondary Metabolites and Molecular Differences of Gentiana jentiana [J]. Chinese Journal of Experimental Prespectology, 2016, 022(018):35-39.
10. He Caijing, Wang Jing, Liang Shuai, et al. Exploring the hepatoprotective mechanism of Gentiana macrophylla based on network pharmacology [J]. Chinese Journal of Traditional Chinese Medicine, 2020, v.45(08):79-89.
11. Xiang Xueying, Yang Jianhua, Hu Junping, etc. Study on Extraction and Purification Technology of Cycloether Terpoid Glycoside from Liver-protecting Active Site of Gentiana in Xinjiang [J]. Northwest Pharmaceutical Journal, 2019, 34(02):151-158.
12. Han Duo, Zhao Zhilian, Liu Weihong, et al. Preliminary Discussion on Quality Evaluation of White Medicinal Plant Gentiana [J]. Traditional Chinese Medicine, 2016, 39(011):2549-2553.
13. Jin Lin, li Haifeng, Liu Weihong, et al. Effects of methyl jasmonate on the contents of four terpenoids in gentian leaves [J]. China Pharmacy, 2019, 030(003):344-348.
14. Wu Xinyi, Liu Xiuqi, Qu Yunhui, Shi Pingping, Yang Yan, Li Zhimin, Tian Hao, Gu Liping. Box-Behnken Design-Response Surface Methodology to Optimize Primary Processing Technology of Gentiana yunnanensis [J]. Chinese pharmacy, 2020,31(15):1830-1835.
15. Tang W, Li W, Yang Y, Lin X, Wang L, Li C, Yang R. Phenolic Compounds Profile and Antioxidant Capacity of Pitahaya Fruit Peel from Two Red-Skinned Species (Hylocereus polyrhizus and Hylocereus undatus). Foods. 2021; 10(6):1183. https://doi.org/10.3390/food
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20. [IF = 4.35] Wanpei Tang et al."Phenolic Compounds Profile and Antioxidant Capacity of Pitahaya Fruit Peel from Two Red-Skinned Species (Hylocereus polyrhizus and Hylocereus undatus)." Foods. 2021 Jun;10(6):1183
21. [IF = 4.225] Huang Xian-ju et al."Veratrilla baillonii Franch Could Alleviate Lipid Accumulation in LO2 Cells by Regulating Oxidative, Inflammatory, and Lipid Metabolic Signaling Pathways." Front Pharmacol. 2020 Sep;0:1511
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(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside

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Hubei YoungXin Pharmaceutical Tech Co.,Ltd.

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Product Name: Gentiopicroside Visit Supplier Webpage Request for quotation
CAS: 20831-76-9
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052

Wechat: 15671228036

Nantong Reform Petro-Chemical CO., LTD.

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Jiangsu Pules Biotechnology Co.,Ltd.

Shanghai Yuanye Bio-Technology Co., Ltd.

Multiple SpecificationsSpot supply

Product Name: Gentiopicroside Visit Supplier Webpage Request for quotation
CAS: 20831-76-9
Tel: 18301782025
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(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside

(5R-trans)-6-(β-D-glucopyranosyloxy)-5,6-dihydro-5-vinyl-1H,3H-pyrano[3,4-c]pyran-1-one

CAS: 20831-76-9

Molecular Formula: C16H20O9

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Names and Identifiers

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Physico-chemical Properties

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Risk and Safety

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Reference

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(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside Request for Quotation

(5R-trans)-6-(β-D-glucopyranosyloxy)-5,6-dihydro-5-vinyl-1H,3H-pyrano[3,4-c]pyran-1-one

CAS: 20831-76-9

Molecular Formula: C16H20O9

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Names and Identifiers

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Physico-chemical Properties

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Risk and Safety

(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside - Reference

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(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside