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MedKoo Cat#: 540155 | Name: Geniposidic acid
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Description:

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

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

Chemical Structure

Geniposidic acid
Geniposidic acid
CAS#27741-01-1

Theoretical Analysis

MedKoo Cat#: 540155

Name: Geniposidic acid

CAS#: 27741-01-1

Chemical Formula: C16H22O10

Exact Mass: 374.1213

Molecular Weight: 374.34

Elemental Analysis: C, 51.34; H, 5.92; O, 42.74

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
250mg USD 1,450.00 2 Weeks
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Related CAS #
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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
Product Data
Instruction
View handling instruction
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/
Solvent mg/mL mM
Solubility
DMF 30.0 80.14
DMSO 48.7 130.01
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 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.
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).

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GSK312948

GSK312948