Geniposidic acid
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MedKoo CAT#: 540155

CAS#: 27741-01-1

Description: Geniposidic acid is a biochemical that promotes collagen synthesis, increases osteoblast proliferation, and inhibits survival of Kalotermes flavicollis and Crematogaster scutellaris.


Chemical Structure

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Geniposidic acid
CAS# 27741-01-1

Theoretical Analysis

MedKoo Cat#: 540155
Name: Geniposidic acid
CAS#: 27741-01-1
Chemical Formula: C16H22O10
Exact Mass: 374.12
Molecular Weight: 374.342
Elemental Analysis: C, 51.34; H, 5.92; O, 42.74

Price and Availability

Size Price Availability Quantity
10mg USD 250 2 Weeks
50mg USD 550 2 Weeks
100mg USD 950 2 Weeks
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Synonym: Geniposidic acid

IUPAC/Chemical Name: (1S,4aS,7aS)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

InChi Key: ZJDOESGVOWAULF-OGJQONSISA-N

InChi Code: InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)/t7-,9-,10-,11-,12+,13-,15+,16+/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@]1([H])CC=C3CO)O

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:
Biological target: Geniposidic acid is an effective anticancer and radioprotection agent.
In vitro activity: GPA pretreatment substantially attenuated LPS-induced NLRP3 expression at both the mRNA and protein levels (Fig. 2A and B and Fig. S2). Furthermore, the release of pro-inflammatory cytokines, including IL-1β, IL-6, and TNF-α, was markedly blunted by GPA pretreatment prior to LPS stimulation (Fig. 2C). Reference: Redox Biol. 2022 Jul 14;55:102404. https://pubmed.ncbi.nlm.nih.gov/35868156/
In vivo activity: The over-expression of LRH-1 in RPH can up-regulate the mRNA and protein levels of CYP7a1. GPA can improve the biochemical and liver pathology of ANIT-induced cholestasis rats, which may be related to the decrease of CYP7a1 by activating SHP through LRH-1 in RPH. Reference: Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2019 Jun 28;44(6):605-613. https://pubmed.ncbi.nlm.nih.gov/31304920/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 80.14
DMSO 48.7 130.01

Preparing Stock Solutions

The following data is based on the product molecular weight 374.34 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. Song M, Chen Z, Qiu R, Zhi T, Xie W, Zhou Y, Luo N, Fuqian Chen, Liu F, Shen C, Lin S, Zhang F, Gao Y, Liu C. Inhibition of NLRP3-mediated crosstalk between hepatocytes and liver macrophages by geniposidic acid alleviates cholestatic liver inflammatory injury. Redox Biol. 2022 Jul 14;55:102404. doi: 10.1016/j.redox.2022.102404. Epub ahead of print. PMID: 35868156; PMCID: PMC9304672. 2. Song M, Chen Z, Qiu R, Zhi T, Xie W, Zhou Y, Luo N, Fuqian Chen, Liu F, Shen C, Lin S, Zhang F, Gao Y, Liu C. Inhibition of NLRP3-mediated crosstalk between hepatocytes and liver macrophages by geniposidic acid alleviates cholestatic liver inflammatory injury. Redox Biol. 2022 Jul 14;55:102404. doi: 10.1016/j.redox.2022.102404. Epub ahead of print. PMID: 35868156; PMCID: PMC9304672. 3. Chen H, Gao X, Zhao W, Yu H, Wang N, Mi S. [Effect of geniposidic acid on SHP-LRH-1 signaling pathway in cholestasis rats]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2019 Jun 28;44(6):605-613. Chinese. doi: 10.11817/j.issn.1672-7347.2019.06.001. PMID: 31304920.
In vitro protocol: 1. Song M, Chen Z, Qiu R, Zhi T, Xie W, Zhou Y, Luo N, Fuqian Chen, Liu F, Shen C, Lin S, Zhang F, Gao Y, Liu C. Inhibition of NLRP3-mediated crosstalk between hepatocytes and liver macrophages by geniposidic acid alleviates cholestatic liver inflammatory injury. Redox Biol. 2022 Jul 14;55:102404. doi: 10.1016/j.redox.2022.102404. Epub ahead of print. PMID: 35868156; PMCID: PMC9304672.
In vivo protocol: 1. Song M, Chen Z, Qiu R, Zhi T, Xie W, Zhou Y, Luo N, Fuqian Chen, Liu F, Shen C, Lin S, Zhang F, Gao Y, Liu C. Inhibition of NLRP3-mediated crosstalk between hepatocytes and liver macrophages by geniposidic acid alleviates cholestatic liver inflammatory injury. Redox Biol. 2022 Jul 14;55:102404. doi: 10.1016/j.redox.2022.102404. Epub ahead of print. PMID: 35868156; PMCID: PMC9304672. 2. Chen H, Gao X, Zhao W, Yu H, Wang N, Mi S. [Effect of geniposidic acid on SHP-LRH-1 signaling pathway in cholestasis rats]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2019 Jun 28;44(6):605-613. Chinese. doi: 10.11817/j.issn.1672-7347.2019.06.001. PMID: 31304920.

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1. Carrillo-Ocampo, D., Bazaldúa-Gómez, S., Bonilla-Barbosa, J.R., et al. Anti-inflammatory activity of iridoids and verbascoside isolated from Castilleja tenuiflora. Molecules 18(10), 12109-12118 (2013).

2. Kim, S.-J., Kim, K.-M., Park, J., et al. Geniposidic acid protects against D-galactosamine and lipopolysaccharide-induced hepatic failure in mice. J. Ethnopharmacol. 146(1), 271-277 (2013).

3. Nakamura, K., Hosoo, S., Yamaguchi, S., et al. Geniposidic acid upregulates atrial natriuretic peptide secretion and lowers blood pressure in spontaneously hypertensive rat. J. Funct. Foods 40, 634-638 (2018).