Geniposide
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MedKoo CAT#: 600139

CAS#: 24512-63-8

Description: 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

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Geniposide
CAS# 24512-63-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 600139
Name: Geniposide
CAS#: 24512-63-8
Chemical Formula: C17H24O10
Exact Mass: 388.14
Molecular Weight: 388.369
Elemental Analysis: C, 52.57; H, 6.23; O, 41.20

Price and Availability

Size Price Availability Quantity
100mg USD 300 2 Weeks
250mg USD 550 2 Weeks
500mg USD 950
1g USD 1650
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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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. 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

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.

Recalculate based on batch purity %
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: 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.
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.

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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.