Geniposide | CAS#24512-63-8 | MedKoo Biosciences

MedKoo Cat#: 600139 | Name: Geniposide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Geniposide is a natural product isolated from the fruit of Gerdenia. It was found to induce increased activity of phase II detoxifying enzymes, inhibit tumor promotion, and induce apoptosis in rat C6 glioma cells. (Source: http://www.lktlabs.com/products/Geniposide-816-12.html).

Chemical Structure

Geniposide

CAS#24512-63-8

Theoretical Analysis

MedKoo Cat#: 600139

Name: Geniposide

CAS#: 24512-63-8

Chemical Formula: C17H24O10

Exact Mass: 388.1370

Molecular Weight: 388.37

Elemental Analysis: C, 52.57; H, 6.23; O, 41.20

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
250mg	USD 650.00	2 Weeks
500mg	USD 950.00	2 Weeks
1g	USD 1,350.00	2 Weeks

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Synonym

Geniposide

IUPAC/Chemical Name

Methyl (1R,2S,6S)-9-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate

InChi Key

IBFYXTRXDNAPMM-VDNSNXDHSA-N

InChi Code

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

SMILES Code

O=C(C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@]3([H])C(CO)=CC[C@]13[H])OC

Appearance

solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Geniposide is an iridoid glucoside extracted from Gardenia jasminoides Ellis fruits; exhibits a varity of biological activities such as anti-diabetic, antioxidative, antiproliferative and neuroprotective activities.

In vitro activity:

Considering the results that geniposide alleviates H/R injury in vitro and AMPK was also related to H/R-induced cardiac cell injury, geniposide protected against H/R injury in a dose-dependent way. In contrast, co-culture of Compound C with geniposide completely blocked these protective actions (Fig. 4C). Moreover, to determine whether geniposide attenuates H/R-induced mitochondrial dysfunction, MMP levels were increased. Reference: Chin Med. 2022 Jun 17;17(1):73. https://pubmed.ncbi.nlm.nih.gov/35715805/

In vivo activity:

In all diabetic rats, the blood glucose levels increased significantly. After oral administration of geniposide, the blood glucose level significantly decreased on day 7 after continuous administration compared to the model group (Figure 1, p < 0.05), whilst the level of HbA1c was not changed in treatment subgroups. Reference: Pharm Biol. 2022 Dec;60(1):294-299. https://pubmed.ncbi.nlm.nih.gov/35130118/

	Solvent	mg/mL	mM
Solubility
	DMF	15.0	38.62
	DMSO	69.3	178.52
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.85
	Water	64.0	164.79

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 388.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Li H, Yang DH, Zhang Y, Zheng F, Gao F, Sun J, Shi G. Geniposide suppresses NLRP3 inflammasome-mediated pyroptosis via the AMPK signaling pathway to mitigate myocardial ischemia/reperfusion injury. Chin Med. 2022 Jun 17;17(1):73. doi: 10.1186/s13020-022-00616-5. PMID: 35715805; PMCID: PMC9205109. 2. Shen Y, Wang X, Shen X, Wang Y, Wang S, Zhang Y, Yao X, Xu Y, Sang M, Pan J, Qin Y, Zhou Q, Shen J. Geniposide Possesses the Protective Effect on Myocardial Injury by Inhibiting Oxidative Stress and Ferroptosis via Activation of the Grsf1/GPx4 Axis. Front Pharmacol. 2022 May 5;13:879870. doi: 10.3389/fphar.2022.879870. PMID: 35600863; PMCID: PMC9117627. 3. Chen XY, Jiang WW, Liu YL, Ma ZX, Dai JQ. Anti-inflammatory action of geniposide promotes wound healing in diabetic rats. Pharm Biol. 2022 Dec;60(1):294-299. doi: 10.1080/13880209.2022.2030760. PMID: 35130118; PMCID: PMC8823683. 4. Zheng Y, Xiao Y, Zhang D, Zhang S, Ouyang J, Li L, Shi W, Zhang R, Liu H, Jin Q, Chen Z, Xu D, Wu L. Geniposide Ameliorated Dexamethasone-Induced Cholesterol Accumulation in Osteoblasts by Mediating the GLP-1R/ABCA1 Axis. Cells. 2021 Dec 6;10(12):3424. doi: 10.3390/cells10123424. PMID: 34943934; PMCID: PMC8699812.

In vitro protocol:

In vivo protocol:

1. Chen XY, Jiang WW, Liu YL, Ma ZX, Dai JQ. Anti-inflammatory action of geniposide promotes wound healing in diabetic rats. Pharm Biol. 2022 Dec;60(1):294-299. doi: 10.1080/13880209.2022.2030760. PMID: 35130118; PMCID: PMC8823683. 2. Zheng Y, Xiao Y, Zhang D, Zhang S, Ouyang J, Li L, Shi W, Zhang R, Liu H, Jin Q, Chen Z, Xu D, Wu L. Geniposide Ameliorated Dexamethasone-Induced Cholesterol Accumulation in Osteoblasts by Mediating the GLP-1R/ABCA1 Axis. Cells. 2021 Dec 6;10(12):3424. doi: 10.3390/cells10123424. PMID: 34943934; PMCID: PMC8699812.

1: Yao DD, Shu L, Yang L, Jia XB. [Advance in studies on anti-diabetic mechanism of Gardeniae Fructus and its active ingredient geniposide]. Zhongguo Zhong Yao Za Zhi. 2014 Apr;39(8):1368-73. Review. Chinese. PubMed PMID: 25039166.