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MedKoo Cat#: 326774 | Name: Genipin
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Description:

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

Genipin is a natural compound isolated from Gardenis jasminoides Ellis fruits, was originally identified as a protein cross-linking agent. Genipin ameliorates hypertension-induced renal damage via the angiotensin II-TLR/MyD88/MAPK pathway. genipin shows therapeutic potential for central neurodegenerative diseases. IRE1α inhibition by natural compound genipin on tumour associated macrophages reduces growth of hepatocellular carcinoma.

Chemical Structure

Genipin
Genipin
CAS#6902-77-8

Theoretical Analysis

MedKoo Cat#: 326774

Name: Genipin

CAS#: 6902-77-8

Chemical Formula: C11H14O5

Exact Mass: 226.0841

Molecular Weight: 226.23

Elemental Analysis: C, 58.40; H, 6.24; O, 35.36

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
250mg USD 450.00 2 Weeks
500mg USD 750.00 2 Weeks
1g USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Genipin; (+)-Genipin
IUPAC/Chemical Name
Methyl (1S,2R,6S)-2-Hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
InChi Key
AZKVWQKMDGGDSV-BCMRRPTOSA-N
InChi Code
InChI=1S/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1
SMILES Code
O=C(C1=CO[C@@H](O)[C@]2([H])C(CO)=CC[C@]12[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:
Genipin inhibits UCP2 (uncoupling protein 2) in cells.
In vitro activity:
In conclusion, genipin showed anti-inflammatory and antiviral activities against rotavirus in vitro and in vivo, which led to significantly reduced diarrhea incidence and suppressed viral shedding, by inhibiting the replication cycle (Fig. 8). Reference: Sci Rep. 2020 Sep 28;10(1):15836. doi: 10.1038/s41598-020-72968-7. https://pubmed.ncbi.nlm.nih.gov/32985574/
In vivo activity:
This study found marked atrophy of the seminiferous tubules and more vacuoles in the SC (disrupted + saline) group than in the NC (normal control) group, whereas genipin treatment alleviated this damage (Fig. 2b). The average numbers of spermatogonia and spermatids were reduced significantly in male SC mice (p < 0.05) compared with male NC mice, and genipin treatment reestablished these effects on these cells (Fig. 2d and e). Reference: Reprod Biol Endocrinol. 2020 Dec 11;18(1):122. https://pubmed.ncbi.nlm.nih.gov/33308222/
Solvent mg/mL mM
Solubility
DMF 25.0 110.51
DMSO 65.0 287.32
DMSO:PBS (pH 7.2) (1:3) 0.3 1.11
Ethanol 25.0 110.51
Water 2.5 11.05
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 226.23 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. Kim JH, Kim K, Kim W. Genipin inhibits rotavirus-induced diarrhea by suppressing viral replication and regulating inflammatory responses. Sci Rep. 2020 Sep 28;10(1):15836. doi: 10.1038/s41598-020-72968-7. PMID: 32985574; PMCID: PMC7522720. 2. Kim HJ, Nam YR, Woo J, Kim WK, Nam JH. Gardenia jasminoides extract and its constituent, genipin, inhibit activation of CD3/CD28 co-stimulated CD4+ T cells via ORAI1 channel. Korean J Physiol Pharmacol. 2020 Jul 1;24(4):363-372. doi: 10.4196/kjpp.2020.24.4.363. PMID: 32587130; PMCID: PMC7317176. 3. Xu W, Chen Q, Zhang X, Zhao Y, Wu S, Yang C, Liu Y, Liang L, Jia D, Li C, Fan L, Shi Y. Genipin protects against mitochondrial damage of the retinal pigment epithelium under hyperglycemia through the AKT pathway mediated by the miR-4429/JAK2 signaling axis. Ann Transl Med. 2022 May;10(10):587. doi: 10.21037/atm-22-2219. PMID: 35722358; PMCID: PMC9201119. 4. Xu Y, Wang L, Cao S, Hu R, Liu R, Hua K, Guo Z, Di HJ, Hu Z. Genipin improves reproductive health problems caused by circadian disruption in male mice. Reprod Biol Endocrinol. 2020 Dec 11;18(1):122. doi: 10.1186/s12958-020-00679-9. PMID: 33308222; PMCID: PMC7731552.
In vitro protocol:
1. Kim JH, Kim K, Kim W. Genipin inhibits rotavirus-induced diarrhea by suppressing viral replication and regulating inflammatory responses. Sci Rep. 2020 Sep 28;10(1):15836. doi: 10.1038/s41598-020-72968-7. PMID: 32985574; PMCID: PMC7522720. 2. Kim HJ, Nam YR, Woo J, Kim WK, Nam JH. Gardenia jasminoides extract and its constituent, genipin, inhibit activation of CD3/CD28 co-stimulated CD4+ T cells via ORAI1 channel. Korean J Physiol Pharmacol. 2020 Jul 1;24(4):363-372. doi: 10.4196/kjpp.2020.24.4.363. PMID: 32587130; PMCID: PMC7317176.
In vivo protocol:
1. Xu W, Chen Q, Zhang X, Zhao Y, Wu S, Yang C, Liu Y, Liang L, Jia D, Li C, Fan L, Shi Y. Genipin protects against mitochondrial damage of the retinal pigment epithelium under hyperglycemia through the AKT pathway mediated by the miR-4429/JAK2 signaling axis. Ann Transl Med. 2022 May;10(10):587. doi: 10.21037/atm-22-2219. PMID: 35722358; PMCID: PMC9201119. 2. Xu Y, Wang L, Cao S, Hu R, Liu R, Hua K, Guo Z, Di HJ, Hu Z. Genipin improves reproductive health problems caused by circadian disruption in male mice. Reprod Biol Endocrinol. 2020 Dec 11;18(1):122. doi: 10.1186/s12958-020-00679-9. PMID: 33308222; PMCID: PMC7731552.
1: Shen XL, Liu H, Xiang H, Qin XM, Du GH, Tian JS. Combining biochemical with (1)H NMR-based metabolomics approach unravels the antidiabetic activity of genipin and its possible mechanism. J Pharm Biomed Anal. 2016 Jun 25;129:80-89. doi: 10.1016/j.jpba.2016.06.041. [Epub ahead of print] PubMed PMID: 27411170. 2: Li Y, Li L, Hölscher C. Therapeutic Potential of Genipin in Central Neurodegenerative Diseases. CNS Drugs. 2016 Jul 9. [Epub ahead of print] PubMed PMID: 27395402. 3: Yu D, Shi M, Bao J, Yu X, Li Y, Liu W. Genipin ameliorates hypertension-induced renal damage via the angiotensin II-TLR/MyD88/MAPK pathway. Fitoterapia. 2016 Jul;112:244-53. doi: 10.1016/j.fitote.2016.06.010. Epub 2016 Jun 23. PubMed PMID: 27343367. 4: Jiang P, Ma Y, Gao Y, Li Z, Lian S, Xu Z, Jiang W, Tian X, Huang C. Comprehensive Evaluation of the Metabolism of Genipin-1-β-d-gentiobioside in Vitro and in Vivo by Using HPLC-Q-TOF. J Agric Food Chem. 2016 Jul 13;64(27):5490-8. doi: 10.1021/acs.jafc.6b01835. Epub 2016 Jun 30. PubMed PMID: 27302600. 5: Tan HY, Wang N, Tsao SW, Che CM, Yuen MF, Feng Y. IRE1α inhibition by natural compound genipin on tumour associated macrophages reduces growth of hepatocellular carcinoma. Oncotarget. 2016 May 30. doi: 10.18632/oncotarget.9696. [Epub ahead of print] PubMed PMID: 27270308. 6: Zhang A, Wang S, Zhang J, Wu H. Genipin alleviates LPS-induced acute lung injury by inhibiting NF-κB and NLRP3 signaling pathways. Int Immunopharmacol. 2016 Jun 2;38:115-119. doi: 10.1016/j.intimp.2016.05.011. [Epub ahead of print] PubMed PMID: 27262946. 7: Huang GQ, Cheng LY, Xiao JX, Wang SQ, Han XN. Genipin-crosslinked O-carboxymethyl chitosan-gum Arabic coacervate as a pH-sensitive delivery system and microstructure characterization. J Biomater Appl. 2016 May 26. pii: 0885328216651393. [Epub ahead of print] PubMed PMID: 27231264. 8: Chronopoulou L, Toumia Y, Cerroni B, Pandolfi D, Paradossi G, Palocci C. Biofabrication of genipin-crosslinked peptide hydrogels and their use in the controlled delivery of naproxen. N Biotechnol. 2016 May 7. pii: S1871-6784(16)30010-3. doi: 10.1016/j.nbt.2016.04.006. [Epub ahead of print] PubMed PMID: 27167857. 9: De Clercq K, Schelfhout C, Bracke M, De Wever O, Van Bockstal M, Ceelen W, Remon JP, Vervaet C. Genipin-crosslinked gelatin microspheres as a strategy to prevent postsurgical peritoneal adhesions: In vitro and in vivo characterization. Biomaterials. 2016 Jul;96:33-46. doi: 10.1016/j.biomaterials.2016.04.012. Epub 2016 Apr 22. PubMed PMID: 27135715. 10: Muzzarelli RA, El Mehtedi M, Bottegoni C, Gigante A. Physical properties imparted by genipin to chitosan for tissue regeneration with human stem cells: A review. Int J Biol Macromol. 2016 Apr 19. pii: S0141-8130(16)30234-3. doi: 10.1016/j.ijbiomac.2016.03.075. [Epub ahead of print] Review. PubMed PMID: 27106590. 11: Wang Y, Bao J, Wu X, Wu Q, Li Y, Zhou Y, Li L, Bu H. Genipin crosslinking reduced the immunogenicity of xenogeneic decellularized porcine whole-liver matrices through regulation of immune cell proliferation and polarization. Sci Rep. 2016 Apr 21;6:24779. doi: 10.1038/srep24779. PubMed PMID: 27098308; PubMed Central PMCID: PMC4838870. 12: Fiamingo A, Campana-Filho SP. Structure, morphology and properties of genipin-crosslinked carboxymethylchitosan porous membranes. Carbohydr Polym. 2016 Jun 5;143:155-63. doi: 10.1016/j.carbpol.2016.02.016. Epub 2016 Feb 8. PubMed PMID: 27083355. 13: Sun F, Jiang Y, Xu Y, Shi H, Zhang S, Liu X, Pan S, Ye G, Zhang W, Zhang F, Zhong C. Genipin cross-linked decellularized tracheal tubular matrix for tracheal tissue engineering applications. Sci Rep. 2016 Apr 15;6:24429. doi: 10.1038/srep24429. PubMed PMID: 27080716; PubMed Central PMCID: PMC4832209. 14: Zhang Y, Wang QS, Yan K, Qi Y, Wang GF, Cui YL. Preparation, characterization, and evaluation of genipin crosslinked chitosan/gelatin three-dimensional scaffolds for liver tissue engineering applications. J Biomed Mater Res A. 2016 Aug;104(8):1863-70. doi: 10.1002/jbm.a.35717. Epub 2016 Mar 30. PubMed PMID: 27027247. 15: Zhu SQ, Zheng LY, Pan AP, Yu AY, Wang QM, Xue AQ. The efficacy and safety of posterior scleral reinforcement using genipin cross-linked sclera for macular detachment and retinoschisis in highly myopic eyes. Br J Ophthalmol. 2016 Feb 25. pii: bjophthalmol-2015-308087. doi: 10.1136/bjophthalmol-2015-308087. [Epub ahead of print] PubMed PMID: 26917677. 16: Khan H, Shukla RN, Bajpai AK. Genipin-modified gelatin nanocarriers as swelling controlled drug delivery system for in vitro release of cytarabine. Mater Sci Eng C Mater Biol Appl. 2016 Apr 1;61:457-65. doi: 10.1016/j.msec.2015.12.085. Epub 2015 Dec 30. PubMed PMID: 26838872. 17: Wang R, Zhao J, Zhang L, Peng L, Zhang X, Zheng W, Chen H. Genipin Derivatives Protect RGC-5 from Sodium Nitroprusside-Induced Nitrosative Stress. Int J Mol Sci. 2016 Jan 19;17(1). pii: E117. doi: 10.3390/ijms17010117. PubMed PMID: 26797604; PubMed Central PMCID: PMC4730358. 18: Ghasemi A, Mohtashami M, Sheijani SS, Aliakbari K. Chitosan-genipin nanohydrogel as a vehicle for sustained delivery of alpha-1 antitrypsin. Res Pharm Sci. 2015 Nov-Dec;10(6):523-34. PubMed PMID: 26779272; PubMed Central PMCID: PMC4698863. 19: Yang Y, Yang Y, Hou J, Ding Y, Zhang T, Zhang Y, Wang J, Shi C, Fu W, Cai Z. The Hydroxyl at Position C1 of Genipin Is the Active Inhibitory Group that Affects Mitochondrial Uncoupling Protein 2 in Panc-1 Cells. PLoS One. 2016 Jan 15;11(1):e0147026. doi: 10.1371/journal.pone.0147026. eCollection 2016. PubMed PMID: 26771380; PubMed Central PMCID: PMC4714807. 20: Yao ML, Gu J, Zhang YC, Wang N, Zhu ZH, Yang QT, Liu M, Xia JF. [Inhibitory effect of Genipin on uncoupling protein-2 and energy metabolism of androgen-independent prostate cancer cells]. Zhonghua Nan Ke Xue. 2015 Nov;21(11):973-6. Chinese. PubMed PMID: 26738321.