Cannabichromenic acid, (+)-

Base Information

• Chemical Name: Cannabichromenic acid, (+)-
• CAS No.: 20408-52-0
• Molecular Formula: C22H30O4
• Molecular Weight: 358.478
• UNII: NNW8UMP980,GHH6KX8TQS
• DSSTox Substance ID: DTXSID301336859
• Nikkaji Number: J16.297C,J167.322J
• Wikipedia: Cannabichromenic_acid
• Wikidata: Q27284972
• ChEMBL ID: CHEMBL4594109
• Mol file: 20408-52-0.mol

Synonyms:Cannabichromenic acid;20408-52-0;(+)-Cannabichromenic acid;CBCA;5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromene-6-carboxylic acid;NNW8UMP980;Cannabichromenic acid, (+)-;185505-15-1;GHH6KX8TQS;UNII-NNW8UMP980;(+-)-Cannabichromenic acid;CHEBI:167557;(+/-)-CANNABICHROMENIC ACID;2H-1-Benzopyran-6-carboxylic acid, 5-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-7-pentyl-, (+)-;Cannabichromenic acid (CBCA);2H-1-Benzopyran-6-carboxylic acid, 5-hydroxy-2-methyl-2-(4-methyl-3-penten-1-yl)-7-pentyl-;2H-1-Benzopyran-6-carboxylic acid, 5-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-7-pentyl-;5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromene-6-carboxylic acid;(+)-5-HYDROXY-2-METHYL-2-(4-METHYL-3-PENTEN-1-YL)-7-PENTYL-2H-1-BENZOPYRAN-6-CARBOXYLIC ACID;2H-1-BENZOPYRAN-6-CARBOXYLIC ACID, 5-HYDROXY-2-METHYL-2-(4-METHYL-3-PENTEN-1-YL)-7-PENTYL-, (+)-;UNII-GHH6KX8TQS;SCHEMBL9909325;CHEMBL4594109;DTXSID301336859;(+/-)-CANNABICHROMENIC ACID A;CANNABICHROMENIC ACID, (+/-)-;BC175206;Q27284972;Cannabichromic acid (CBCA) 100 microg/mL in Acetonitrile;Cannabichromic acid (CBCA) 1000 microg/mL in Acetonitrile;5-Hydroxy-2-methyl-2-(4-methyl-3-penten-1-yl)-7-pentyl-2H-1-benzopyran-6-carboxylic acid;5-Hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-1-benzopyran-6-carboxylic acid;2H-1-Benzopyran-6-carboxylic acid, 5-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-7-pentyl-, ()-

Chemical Property of Cannabichromenic acid, (+)-

Chemical Property:

• Vapor Pressure: 4.7E-10mmHg at 25°C
• Boiling Point: 480.8°Cat760mmHg
• Flash Point: 159.5°C
• PSA: 66.76000
• Density: 1.088g/cm³
• LogP: 5.73380
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 358.21440943
• Heavy Atom Count: 26
• Complexity: 534

Purity/Quality:

99%, ^*data from raw suppliers

5-Hydroxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromene-6-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1C(=O)O)O

Technology Process of Cannabichromenic acid, (+)-

There total 12 articles about Cannabichromenic acid, (+)- 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:

geranyl diphosphate (763-10-0) → 6-carboxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol (20408-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: aromatic prenyltransferase / Enzymatic reaction

2: cannabichromenic acid synthase / Enzymatic reaction

With cannabichromenic acid synthase; aromatic prenyltransferase;

Reference yield:

2-bromo-1,5-dimethoxy-3-pentyl-benzene (112639-01-7) → 6-carboxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol (20408-52-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: magnesium / tetrahydrofuran / 30 - 40 °C

1.2: 1 h / 35 °C / Reflux

2.1: aluminum (III) chloride / dichloromethane / 20 - 40 °C

3.1: piperidine / toluene / 0.5 h / 50 - 55 °C

3.2: Reflux

4.1: alkaline condition

5.1: aminosulfonic acid; water / tetrahydrofuran; dimethyl sulfoxide

6.1: potassium hydroxide; water / methanol

With piperidine; aluminum (III) chloride; aminosulfonic acid; water; magnesium; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene;

Reference yield:

2,4-dimethoxy-6-pentyl-benzaldehyde → 6-carboxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol (20408-52-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aluminum (III) chloride / dichloromethane / 20 - 40 °C

2.1: piperidine / toluene / 0.5 h / 50 - 55 °C

2.2: Reflux

3.1: alkaline condition

4.1: aminosulfonic acid; water / tetrahydrofuran; dimethyl sulfoxide

5.1: potassium hydroxide; water / methanol

With piperidine; aluminum (III) chloride; aminosulfonic acid; water; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene;

upstream raw materials:

CBGA

geranyl diphosphate

2-bromo-1,5-dimethoxy-3-pentyl-benzene

2,4-dihydroxyl-6-pentylbenzaldehyde

Downstream raw materials:

cannabichromene

Refernces

• 1、 Morimoto,Komatsu,Taura,Shoyama. "Enzymological evidence for cannabichromenic acid biosynthesis". . p. 854 - 867. Retrieved 1997.
• 2、 -. "CANNABICHROMENIC ACID SYNTHASE FROM CANNABIS SATIVA". Sheet 1/4. . Retrieved 2016/04/09.