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

MedKoo CAT#: 326774

CAS#: 6902-77-8

Description: 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.


Price and Availability

Size
Price

25mg
USD 150
200mg
USD 850
Size
Price

50mg
USD 250
500mg
USD 1650
Size
Price

100mg
USD 450
1g
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Genipin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326774
Name: Genipin
CAS#: 6902-77-8
Chemical Formula: C11H14O5
Exact Mass: 226.0841
Molecular Weight: 226.228
Elemental Analysis: C, 58.40; H, 6.24; O, 35.36


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


Technical Data

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).

Harmonized System Code:
293490


References

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.