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

CAS: 6902-77-8 Cat. No.: G425537 Formula: C11H14O5 Molecular Weight: 226.23 EC Number: 636-196-5
AVAILABLE TO ORDER
GRADE & PURITY 10mM in DMSO
Synonyms
(1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester | methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate | MFCD00888600 | s2412 | CCG-221820 | AC1L9CSN
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
★
Size
USA
Germany (EU)*
Price
Qty
1ml
G425537-1ml
Made to order · 8–12 wks
$49.90
Enter a quantity for the sizes you want to add.
🧪
Why this grade

10mM in DMSO for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

🌡

Storage & shipping

Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.

📋

Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

📚

Literature proof

Cited in 106 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Overview

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.

Specifications

Synonyms
(1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester | methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate | MFCD00888600 | s2412 | CCG-221820 | AC1L9CSN
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
Store at -80°C
Shipped In
Dry ice packs + Cold packs
This product requires cold chain shipping. Ground and other economy services are not available.
Names and Identifiers
Canonical Smiles
COC(=O)C1=COC(C2C1CC=C2CO)O
IUPAC Name
methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
InChIKey
AZKVWQKMDGGDSV-BCMRRPTOSA-N
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
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=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

<<<<<<< HEAD Download SDS → ======= Download SDS → >>>>>>> release248-p3

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassMonoterpenoids
Intermediate Tree Nodes Not available
Direct ParentIridoids 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 FrameworkAliphatic 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
DescriptionThis 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
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
PTPN2 Tchem T-cell protein-tyrosine phosphatase (1317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ARSA Tbio Cerebroside-sulfatase (655 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTPN11 Tchem Protein-tyrosine phosphatase 2C (2297 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGS (1999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Raji (5516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CD81 Tchem CD81 antigen (15 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EGR1 Tbio Early growth response protein 1 (24 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hepatitis C virus (23859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterovirus A71 (1246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bulinus africanus (4 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
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 Weight226.230 g/mol
XLogP3-0.700
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass226.084 Da
Monoisotopic Mass226.084 Da
Topological Polar Surface Area76.000 Ų
Heavy Atom Count16
Formal Charge0
Complexity357.000
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Documents & Articles
Genipin
Research Value of Polyelectrolyte Multilayers: Layer-by-Layer Design of Interfacial Composition, Mass Transport, and Function
Key Judgments in Medical Hydrogel R&D: From Polymer Source and Crosslinking Strategy to Sterilization Planning, Scale-Up Feasibility, and Quality Control
From Natural Cellulose to Nanocrystals: Structural Characteristics, Application Directions, and Industrialization Challenges of CNC
What Determines Collagen Function: From Triple-Helix Formation to Hierarchical Assembly, Crosslink Maturation, and Dynamic Remodeling
Differences Between Animal-Derived Collagen and Recombinant Collagen in Skincare: Sequence and Structure, Safety, Skin Effects, and Evidence Evaluation
Citations of This Product
Solution Calculators
Reviews

Customer Reviews

Frequently Asked Questions

How should this product be stored?
Store at ?80 °C. Ultra-low temperature storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 6902-77-8, the molecular formula is C11H14O5, and the molecular weight is 226.23 g/mol. InChIKey AZKVWQKMDGGDSV-BCMRRPTOSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.

Shall we send you a message when we have discounts available?

Remind me later

Thank you! Please check your email inbox to confirm.

Oops! Notifications are disabled.