Geniposide information

Geniposide
Names
	IUPAC name Methyl (1S,4aS,7aS)-1-(β-D-glucopyranosyloxy)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
	Systematic IUPAC name Methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
	Other names Jasminoidin; methyl 1-(hexopyranosyloxy)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Identifiers
CAS Number	24512-63-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5299 ;
ChEMBL	ChEMBL462894 ;
ChemSpider	96987 ;
ECHA InfoCard	100.208.687
EC Number	683-175-1;
KEGG	C09781 ;
MeSH	geniposide
PubChem CID	107848;
UNII	145295QLXY ;
CompTox Dashboard (EPA)	DTXSID101318419 ;
	InChI InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1 Key: IBFYXTRXDNAPMM-BVTMAQQCSA-N ;
	SMILES COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)CO)O)O)O;
Properties
Chemical formula	C17H24O10
Molar mass	388.369 g·mol−1
Melting point	245.23 °C (473.41 °F; 518.38 K)
Boiling point	641.4±55.0 °C at 760 mmHg
log P	-1.854
Acidity (pKa)	12.80±0.70
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301
Precautionary statements	P264, P270, P301+P310, P321, P330, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). (what is ?) Infobox references

Geniposide, the glycoside form of genipin, is a bioactive iridoid glycoside that is found in a wide variety of medicinal herbs, such as Gardenia jasminoides (fruits) .^[2] Geniposide shows several pharmacological effects (in vitro and in vivo) including neuroprotective, antidiabetic, hepatoprotective, anti-inflammatory, analgesic, antidepressant-like, cardioprotective, antioxidant, immune-regulatory, antithrombotic and antitumoral activity.^[3] These pharmacology benefits arise through the modulating action of geniposide on several proteins and genes that are associated with inflammatory and oxidative stress processes.^[4]

^ CID 387043706 from PubChem
^ Zhou YX, Zhang RQ, Rahman K, Cao ZX, Zhang H, Peng C (April 2019). "Diverse Pharmacological Activities and Potential Medicinal Benefits of Geniposide". Evidence-Based Complementary and Alternative Medicine. 2019: 4925682. doi:10.1155/2019/4925682. PMC 6500620. PMID 31118959.
^ Cite error: The named reference shan2015 was invoked but never defined (see the help page).
^ Li N, Li L, Wu H, Zhou H (April 2019). "Antioxidative Property and Molecular Mechanisms Underlying Geniposide-Mediated Therapeutic Effects in Diabetes Mellitus and Cardiovascular Disease". Oxidative Medicine and Cellular Longevity. 2019: 7480512. doi:10.1155/2019/7480512. PMC 6476013. PMID 31089416.

[1] CID 387043706 from PubChem

[zhou2019-2] Zhou YX, Zhang RQ, Rahman K, Cao ZX, Zhang H, Peng C (April 2019). "Diverse Pharmacological Activities and Potential Medicinal Benefits of Geniposide". Evidence-Based Complementary and Alternative Medicine. 2019: 4925682. doi:10.1155/2019/4925682. PMC 6500620. PMID 31118959.

[shan2015-3] Cite error: The named reference shan2015 was invoked but never defined (see the help page).

[4] Li N, Li L, Wu H, Zhou H (April 2019). "Antioxidative Property and Molecular Mechanisms Underlying Geniposide-Mediated Therapeutic Effects in Diabetes Mellitus and Cardiovascular Disease". Oxidative Medicine and Cellular Longevity. 2019: 7480512. doi:10.1155/2019/7480512. PMC 6476013. PMID 31089416.

Geniposide information

and 6 Related for: Geniposide information

Geniposide

Saffron

Genipin

C17H24O10

Gardenia jasminoides

Penstemon teucrioides

Names

IUPAC name Methyl (1S,4aS,7aS)-1-(β-D-glucopyranosyloxy)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Systematic IUPAC name Methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Other names Jasminoidin;^[1] methyl 1-(hexopyranosyloxy)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Identifiers
CAS Number	24512-63-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5299^Y
ChEMBL	ChEMBL462894^Y
ChemSpider	96987^Y
ECHA InfoCard	100.208.687
EC Number	683-175-1
KEGG	C09781^Y
MeSH	geniposide
PubChem CID	107848
UNII	145295QLXY^Y
CompTox Dashboard (EPA)	DTXSID101318419
InChI InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1 Key: IBFYXTRXDNAPMM-BVTMAQQCSA-N^Y
SMILES COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)CO)O)O)O
Properties
Chemical formula	C₁₇H₂₄O₁₀
Molar mass	388.369 g·mol⁻¹
Melting point	245.23 °C (473.41 °F; 518.38 K)
Boiling point	641.4±55.0 °C at 760 mmHg
log P	-1.854
Acidity (pK_a)	12.80±0.70
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301
Precautionary statements	P264, P270, P301+P310, P321, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is ^YN ?) Infobox references