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6902-77-8

Basic Information
CAS No.: 6902-77-8
Name: 1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester
Article Data: 17
Molecular Structure:
Molecular Structure of 6902-77-8 (1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester)
Formula: C11H14O5
Molecular Weight: 226.229
Synonyms: Cyclopenta[c]pyran-4-carboxylicacid, 1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester, [1R-(1a,4aa,7aa)]-;Cyclopenta[c]pyran-4-carboxylic acid, 1,4aa,5,7aa-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester (8CI);Genipin(6CI);(+)-Genipin;
EINECS: 300-006-4
Density: 1.35 g/cm3
Melting Point: 106-108°C(lit.)
Boiling Point: 416 °C at 760 mmHg
Flash Point: 164.9 °C
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 22
Transport Information: UN 2811 6.1/PG 3
PSA: 75.99000
LogP: -0.05330
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    GENIPIN Basic information Product Name: GENIPIN Synonyms: Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate;cyclopenta(c)pyran-4-carboxylicacid,1,4a-alpha,5,7a-alpha-tetrahydro-1-hydrox;GENIPIN;1,4a,

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Specification

The IUPAC name of Genipin is methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate . With the CAS registry number 6902-77-8, it is also named as Cyclopenta(c)pyran-4-carboxylic acid, 1,4a-alpha,5,7a-alpha-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester .

The Genipin can be found in the gardenia fruit extract. It is is used to relieve the symptoms of type 2 diabetes in traditional Chinese medicine. Research indicated that this product is indeed effective. This research is conducted at the Beth Israel Deaconess Medical Center and Harvard Medical School . It is also used as a cross-linking agent for immobilized enzyme, the raw materials for gardenia blue pigment preparation, the regulating agent for drug delivery, as well as the intermediate for alkaloid synthetic etc.

The Genipin  is poison by ingestion, intravenous, and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes. Do not breathe dust.

The other characteristics of this product can be summarized as: (1)#H bond acceptors: 5 ; (2)#H bond donors: 2 ; (3)#Freely Rotating Bonds: 5 ; (4)Index of Refraction: 1.564 ; (5)Molar Refractivity: 54.52 cm3 ; (6)Molar Volume: 167.4 cm3 ; (7)Polarizability: 21.61×10-24 cm3 ; (8)Surface Tension: 53.5 dyne/cm ; (9)Enthalpy of Vaporization: 77.3 kJ/mol ; (10)Vapour Pressure: 1.17E-08 mmHg at 25°C ; (11)Rotatable Bond Count: 3 ; (12)Exact Mass: 226.084124 ; (13)MonoIsotopic Mass: 226.084124 ; (14)Topological Polar Surface Area: 76 ; (15)Heavy Atom Count: 16.

People can use the following data to convert to the molecule structure. SMILES: O=C(OC)\C1=C\O[C@@H](O)[C@@H]2\C(=C/C[C@H]12)CO; InChI: InChI=1/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.

The following is the toxicity data which has been tested. 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 190mg/kg (190mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 157, 1974.
mouse LD50 intravenous 153mg/kg (153mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 157, 1974.
mouse LD50 oral 237mg/kg (237mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 157, 1974.
rat LD oral > 50mg/kg (50mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 19, Pg. 259, 1980.