MedKoo Cat#: 112026 | Name: Genipin-1-β-D-gentiobioside
Featured

Description:

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

Genipin 1-gentiobioside is an iridoid glycoside that has been found in G. jasminoides and has diverse biological activities. It inhibits acetylcholinesterase (AChE) by 60.23% when used at a concentration of 25 µg/ml. Genipin 1-gentiobioside (50-500 µg/ml) is cytotoxic to BRL 3A rat liver fibroblasts. It inhibits the germination of G. jasminoides and N. offinicale seeds and the growth of B. rapa roots. Genipin 1-gentiobioside (2.5 mg/kg) prevents scopolamine-induced increases in escape latency in the Morris water maze in mice.

Chemical Structure

Genipin-1-β-D-gentiobioside
Genipin-1-β-D-gentiobioside
CAS#29307-60-6

Theoretical Analysis

MedKoo Cat#: 112026

Name: Genipin-1-β-D-gentiobioside

CAS#: 29307-60-6

Chemical Formula: C23H34O15

Exact Mass: 550.1898

Molecular Weight: 550.51

Elemental Analysis: C, 50.18; H, 6.23; O, 43.59

Price and Availability

Size Price Availability Quantity
25mg USD 450.00 2 Weeks
50mg USD 750.00 2 Weeks
100mg USD 1,250.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Genipin 1-gentiobioside; genipin gentiobioside; genipin-1-b-D-gentiobioside; Genipin 1-o-beta-D-gentiobioside; Genipin 1-beta-gentiobioside; Genipin-1-O-gentiobioside
IUPAC/Chemical Name
methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
InChi Key
FYZYXYLPBWLLGI-AUOPOVQUSA-N
InChi Code
InChI=1S/C23H34O15/c1-33-20(32)10-6-34-21(13-8(4-24)2-3-9(10)13)38-23-19(31)17(29)15(27)12(37-23)7-35-22-18(30)16(28)14(26)11(5-25)36-22/h2,6,9,11-19,21-31H,3-5,7H2,1H3/t9-,11-,12-,13-,14-,15-,16+,17+,18-,19-,21+,22-,23+/m1/s1
SMILES Code
COC(C1=CO[C@@H](O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@]4([C@@]1(CC=C4CO)[H])[H])=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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Solvent mg/mL mM
Solubility
DMF 3.0 5.45
DMSO 5.0 9.08
PBS (pH:7.2) 5.0 9.08
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 550.51 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
1: Liu F, Li Y, Li M, Wang J, Zhang Y, Du Y, Yang Y. Study on Mechanism of Iridoid Glycosides Derivatives from Fructus Gardeniae in Jiangxi Province by Network Pharmacology. Evid Based Complement Alternat Med. 2020 Jun 26;2020:4062813. doi: 10.1155/2020/4062813. PMID: 32714404; PMCID: PMC7336235. 2: Li C, Lan M, Lv J, Zhang Y, Gao X, Gao X, Dong L, Luo G, Zhang H, Sun J. Screening of the Hepatotoxic Components in Fructus Gardeniae and Their Effects on Rat Liver BRL-3A Cells. Molecules. 2019 Oct 30;24(21):3920. doi: 10.3390/molecules24213920. PMID: 31671698; PMCID: PMC6864725. 3: Oshima T, Sagara K, Yoshida T, Tong YY, Zhang GD, Chen YH. Determination of geniposide, gardenoside, geniposidic acid and genipin-1-beta-gentiobioside in Gardenia jasminoides by high-performance liquid chromatography. J Chromatogr. 1988 Nov 25;455:410-4. doi: 10.1016/s0021-9673(01)82148-8. PMID: 3235620. 4: Chang R, Liu J, Luo Y, Huang T, Li Q, Wen J, Chen W, Zhou T. Isoflavones' effects on pharmacokinetic profiles of main iridoids from Gardeniae Fructus in rats. J Pharm Anal. 2020 Dec;10(6):571-580. doi: 10.1016/j.jpha.2019.11.004. Epub 2019 Nov 14. PMID: 33425451; PMCID: PMC7775847. 5: Shan MQ, Wang TJ, Jiang YL, Yu S, Yan H, Zhang L, Wu QN, Geng T, Huang WZ, Wang ZZ, Xiao W. Comparative analysis of sixteen active compounds and antioxidant and anti-influenza properties of Gardenia jasminoides fruits at different times and application to the determination of the appropriate harvest period with hierarchical cluster analysis. J Ethnopharmacol. 2019 Apr 6;233:169-178. doi: 10.1016/j.jep.2019.01.004. Epub 2019 Jan 9. PMID: 30639058. 6: Han DE, Yue ZS, Li HW, Liu GZ, Cai BR, Tian P. [Anti-depressant components and mechanism of Rehmanniae Radix based on UPLC-Q-Orbitrap HRMS and network pharmacology]. Zhongguo Zhong Yao Za Zhi. 2022 Feb;47(4):1051-1063. Chinese. doi: 10.19540/j.cnki.cjcmm.20210811.404. PMID: 35285206.