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Genipin - 10mM in DMSO, high purity , CAS No.6902-77-8

    Grade & Purity:
  • 10mM in DMSO
In stock
Item Number
G425537
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G425537-1ml
1ml
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$49.90

Cell-permeable uncoupling protein 2 inhibitor

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Compound libraries (12325)

Basic Description

Synonyms Genipin | 6902-77-8 | (+)-Genipin | CHEBI:5298 | A3V2NE52YG | ST080860 | methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate | C09780 | methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-car
Specifications & Purity 10mM in DMSO
Biochemical and Physiological Mechanisms Genipin stimulates insulin secretion in UCP2-dependent manner (Uncoupling protein 2). Genipin is a protein, collagen, gelatin, and chitosan cross-linker.Cell-permeable uncoupling protein 2 (UCP2) inhibitor. Anti-inflammatory, anti-angiogenic and pro-apoto
Storage Temp Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Product Description

Genipin is a natural cross linking agent, which is extracted from gardenia fruit.It prevents lipid peroxidation and production of nitric oxide. Genipin protects the hippocampal neurons from the toxicity of Alzheimer′s amyloid β protein. It has anti-inflammatory and anti-angiogenesis effects. Genipin is involved in drug delivery system.

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Lipids and lipid-like molecules
Class Prenol lipids
Subclass Monoterpenoids
Intermediate Tree Nodes Not available
Direct Parent Iridoids and derivatives
Alternative Parents Bicyclic monoterpenoids  Vinylogous esters  Methyl esters  Enoate esters  Hemiacetals  Oxacyclic compounds  Monocarboxylic acids and derivatives  Primary alcohols  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular Framework Aliphatic heteropolycyclic compounds
Substituents Iridoid-skeleton - Bicyclic monoterpenoid - Methyl ester - Vinylogous ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Hemiacetal - Carboxylic acid derivative - Oxacycle - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Alcohol - Organic oxygen compound - Organooxygen compound - Primary alcohol - Carbonyl group - Aliphatic heteropolycyclic compound
Description This compound belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.
External Descriptors Iridoids

Associated Targets(Human)

PTPN2 Tchem T-cell protein-tyrosine phosphatase (1317 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ARSA Tbio Cerebroside-sulfatase (655 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PTPN11 Tchem Protein-tyrosine phosphatase 2C (2297 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
AGS (1999 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Raji (5516 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HEK293 (82097 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CD81 Tchem CD81 antigen (15 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
EGR1 Tbio Early growth response protein 1 (24 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Hepatitis C virus (23859 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Enterovirus A71 (1246 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
RAW264.7 (28094 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Bulinus africanus (4 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
INCHI 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
InChIKey AZKVWQKMDGGDSV-BCMRRPTOSA-N
Smiles COC(=O)C1=COC(C2C1CC=C2CO)O
Isomeric SMILES COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O
WGK Germany 3
RTECS GY5828000
UN Number 2811
Molecular Weight 226.23
Reaxy-Rn 2699573
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2699573&ln=

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Specific Rotation[α] +134 to +142 deg(C=1,MeOH)
Melt Point(°C) 121 °C
Molecular Weight 226.230 g/mol
XLogP3 -0.700
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 5
Rotatable Bond Count 3
Exact Mass 226.084 Da
Monoisotopic Mass 226.084 Da
Topological Polar Surface Area 76.000 Ų
Heavy Atom Count 16
Formal Charge 0
Complexity 357.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 3
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 0
Covalently-Bonded Unit Count 1

Citations of This Product

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57. Xiaomei Dai, Meijuan Yuan, Yuxia Yang, Mengbo Dang, Jian Yang, Junli Shi, Dianwei Liu, Mingjun Li, Hang Yao, Wenyong Fei.  (2024)  Dual cross-linked COL1/HAp bionic gradient scaffolds containing human amniotic mesenchymal stem cells promote rotator cuff tendon–bone interface healing.  Biomaterials Advances,  158  (213799). 
58. Liu Wenxiu, Han Guojiang, Qin Liying, Dong Wenli, Han Baoqin, Jin Liming, Yang Yan.  (2024)  Fabrication of bioactive glass/phosphorylated chitosan composite scaffold and its effects on MC3T3-E1 cells.  Biomedical Materials,  19  (2): (025002). 
59. Fang Zhao, Yuxuan Su, Hong Liu, Yong Zhao, Liao Zhang, Nanshan Zhuge, Peng Zhao, Zhaoliang Ning, Qi Kang, Dongxu Liu.  (2025)  Facile Nanocomposite Hydrogel Scaffold with Sustained Drug Release and Osteo-Immunomodulatory Effects to Enhance Bone Regeneration.  ACS Applied Materials & Interfaces,  17  (13): (19286-19303). 
60. Jiaxin Li, Lianghua Xie, Zishan Dou, Yiyang Zhou, Jianling Mo, Wei Chen.  (2024)  Genipin Activates Autophagy and Promotes Myoblast Differentiation by Activating AMPK Pathway.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,  72  (27): (15190-15197). 
61. Ling Wang, Xiaoyue Ding, Jingyu Li, Man Li, Peng Ding, Wei Guo, Qiaoyun Wu, Yanfang Sun, Guohua Jiang, Oseweuba Valentine Okoro, Mahta Mirzaei, Amin Shavandi, Lihong Fan, Lei Nie.  (2024)  Genipin crosslinked quaternary ammonium chitosan hydrogels for wound dressings.  Biomedical Materials,  19  (4): (045042). 
62. Nanting Zhu, Decheng Bi, Jinfeng Huang, Lijun Yao, Yan Wu, Zedong Jiang, Zhangli Hu, Beiwei Zhu, Shuangfei Li, Xu Xu.  (2025)  Genipin crosslinked sodium caseinate-chitosan oligosaccharide nanoparticles for optimizing β-carotene stability and bioavailability.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,    (139626). 
63. Shuai Ma, Li Zhang, Yang Wu, Wei Huang, Fangtian Liu, Mingguang Li, Yifeng Fan, Haibin Xia, Xianguo Wang, Xinzhi Li, Hongbing Deng.  (2024)  Glucosamine sulfate-loaded nanofiber reinforced carboxymethyl chitosan sponge for articular cartilage restoration.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,     
64. Haofu Liu, Zhiqing Huang, Yingyu Shi, Tingyao Cai, Qi Miao, Zideng Gao, Zhenling Cui.  (2024)  Lightweight pH-responsive chitosan hydrogel iron fertilizer: Efficient performance, controlled-release, and tomato application.  Journal of Environmental Chemical Engineering,  12  (113428). 
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