Basic information
- CAS
6902-77-8- Standard SMILES
COC(=O)C1=COC(O)C2C(CO)=CCC12- InChIKey
AZKVWQKMDGGDSV-UHFFFAOYSA-N- Molecular formula
- C11H14O5
- Average molar mass
- 226.23 g/mol
Overview
1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester is an iridoid monoterpenoid.
Names & identifiers
- Preferred name
- Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
- IUPAC
- methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
- English name
- Genipin
- Molecular formula
- C11H14O5
- Molecular weight
- 226.23
Names & synonyms
Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl esterSCHEMBL9609096CHEBI:94318AZKVWQKMDGGDSV-UHFFFAOYSA-NHMS3330G16Cyclopenta[c]pyran-4-carboxylic acid, 1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester, [1R-(1.alpha.,4a.alpha.,7a.alpha.)]-Cyclopenta[c]pyran-4-carboxylic acid, 1,4a.alpha.,5,7a.alpha.-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl esterNSC49633MFCD13185151NSC-49633s2412
Show more names
enipinGENIPINJingpingGenipin>GENIPIN(SH)GENIPIN(RG)(+)-GenipinGenipin(AS)Genipin 95%Genipin, >=98%
AKOS015902656LS-13965BRD-A04308630-001-01-6Q27166138Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate #
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 76 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 357
Experimental & physicochemical properties
Melting Point120 - 121 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 118 to · 118.0 to 123.0 °C
- Boiling point
- 287.83 °C · 287.83°C (rough estimate)
- Density
- 1.123 · 1.1230 (rough estimate)
- refractive index
- 1.472 · 1.4720 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 25 mg/mL · DMSO: ≥25mg/mL
- form
- powder
- pka
- 12.06 · 12.06±0.60(Predicted)
- color
- White to Almost white
- optical activity
- 117.7 ° · 117.7° (C=0.01 g/ml, MEOH)
- λmax
- 240 nm · 240nm(MeOH)(lit.)
- InChI
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- GY5828000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29329990
- risk_code
- 22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn
- safety_code
- 3/14-36/37/39
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P310+P330
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
UsesGenipin is an active aglycone derived from geniposide, an iridoid glycoside found in the fruit of Gardenia jasminoides Ellis. It has been used in traditional Chinese medicine and is a hydrolytic product of geniposide. Genipin is also known for its inhibitory effect on uncoupling protein 2 (UCP2).
UsesGenipin has been used:in chemosensitivity assayin the preparation of recombinant human (rh)-odontogenic ameloblast-associated protein (ODAM) -impregnated collagen gel and in vitro mineralization assayin genipin gel preparation
General DescriptionGenipin 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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Related reactions
3 records
Compound notes
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