Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Base Information

• Chemical Name: Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• CAS No.: 6902-77-8
• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.229
• Hs Code.: 29329990
• NSC Number: 49633
• Wikidata: Q27166138
• Mol file: 6902-77-8.mol

Synonyms:Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate;1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester;1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester;SCHEMBL9609096;CHEBI:94318;AZKVWQKMDGGDSV-UHFFFAOYSA-N;HMS3330G16;BCP27713;Cyclopenta(c)pyran-4-carboxylic acid, 1,4a-alpha,5,7a-alpha-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester;NSC49633;NSC-49633;AKOS015902656;LS-58154;BRD-A04308630-001-01-6;Q27166138;Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate #

Chemical Property of Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Chemical Property:

• Vapor Pressure: 1.17E-08mmHg at 25°C
• Melting Point: 106-108°C(lit.)
• Refractive Index: 1.564
• Boiling Point: 416 °C at 760 mmHg
• PKA: 12.06±0.60(Predicted)
• Flash Point: 164.9 °C
• PSA: 75.99000
• Density: 1.35 g/cm³
• LogP: -0.05330
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO: ≥25mg/mL
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 226.08412354
• Heavy Atom Count: 16
• Complexity: 357

Purity/Quality:

Cape Jasmine Fruit extrac,95% Geniposide ,98% Genipin?, ^*data from raw suppliers

Genipin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 3/14-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=COC(C2C1CC=C2CO)O
• Uses: Genipin is an active aglycone derived from an iridoid glycoside called geniposide, which is found in the fruit of Gardenia jasminoides Ellis. Genipin is a hydrolytic product of geniposide. Genipin has been used in traditional Chinese medicine. Genipin is Genipin is an inhibitor of uncoupling protein 2 (UCP2). Genipin 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

Technology Process of Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

There total 12 articles about Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

geniposide (24512-63-8,27745-20-6) → genipin (70094-79-0,73610-59-0,6902-77-8)

Guidance literature:

With water; In dichloromethane; at 37 ℃; for 24h; Enzymatic reaction;

Reference yield:

choline chloride (67-48-1) + 1,2-dipalmotoyl-3-sn-phosphatidylgenipin → 1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine (2644-64-6,2797-68-4) + genipin (70094-79-0,73610-59-0,6902-77-8)

Guidance literature:

With calcium chloride; In ethyl acetate; Ambient temperature; phospholipase D from Streptomyces sp., acetate buffer, pH 5.6; phospholipase-D-catalysed transphosphatidylation reactions;

Reference yield:

geniposide (24512-63-8,27745-20-6) → β-D-glucose (492-61-5) + genipin (70094-79-0,73610-59-0,6902-77-8)

Guidance literature:

With β-glucosidase from Aspergillus aculeatus; water; In aq. phosphate buffer; at 70 ℃; for 0.333333h; pH=5; Enzymatic reaction;

DOI:10.1016/j.ijbiomac.2018.07.165

upstream raw materials:

geniposide

geniposide

choline chloride

genipin 1-O-β-D-isomaltoside

Downstream raw materials:

1-methoxygenipin

1-benzyloxygenipin

Refernces

• 1、 Chen, Quan Cheng,Zhang, Wei Yun,Youn, UiJoung,Kim, HongJin,Lee, IkSoo,Jung, Hyun-Ju,Na, MinKyun,Min, Byung-Sun,Bae, KiHwan. "Iridoid glycosides from Gardeniae Fructus for treatment of ankle sprain". . p. 779 - 784. Retrieved 2009.
• 2、 Buechi et al.. "". . p. 2776. Retrieved 1967.
• 3、 -. "A PROCESS FOR PRODUCING GARDENIA BLUE PIGMENT FORM GENIPOSIDE". Page/Page column 6. . Retrieved 2018/03/06.
• 4、 -. "BICYCLIC COMPOUND AND PHARMACEUTICAL COMPOSITION THEREOF FOR TREATING STROKE AND USE THEREOF". Paragraph 0095; 0096; 0097; 0098. . Retrieved 2017/11/06.