Agathic acid

Base Information

• Chemical Name: Agathic acid
• CAS No.: 640-28-8
• Molecular Formula: C20H30 O4
• Molecular Weight: 334.456
• Nikkaji Number: J13.565H,J2.540.164F,J916.497I
• Wikidata: Q104394431
• ChEMBL ID: CHEMBL457162
• Mol file: 640-28-8.mol

Synonyms:agathic acid;labda-8(17),13-diene-15,19-dioic acid

Chemical Property of Agathic acid

Chemical Property:

• Vapor Pressure: 3.29E-11mmHg at 25°C
• Boiling Point: 496.5°C at 760 mmHg
• Flash Point: 268.1°C
• PSA: 74.60000
• Density: 1.11g/cm³
• LogP: 4.66100
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 334.21440943
• Heavy Atom Count: 24
• Complexity: 576

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C
• Isomeric SMILES: C/C(=C\C(=O)O)/CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@]2(C)C(=O)O)C

Technology Process of Agathic acid

There total 8 articles about Agathic 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: 100.0%

(E)-15-oxolabda-8(17),13-diene-19-oic acid (159812-25-6) → agathic acid (640-28-8)

Guidance literature:

With sodium chlorite; potassium dihydrogenphosphate; In tert-butyl alcohol; at -5 - 20 ℃; for 15.5h;

DOI:10.1021/jf011501m

Reference yield:

(1S,4aR,5S,8aR)-1,4a-Dimethyl-6-methylene-5-((Z)-3-methyl-5-oxo-pent-3-enyl)-decahydro-naphthalene-1-carboxylic acid → labda-8(17),13(Z)-diene-15,19-dioic acid (640-28-8,17829-02-6,33123-07-8,37886-48-9,41988-89-0,138125-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaCN, AcOH, MnO₂ / Ambient temperature

2: 1 mg / 2percent NaOH / methanol / Ambient temperature

With manganese(IV) oxide; sodium hydroxide; sodium cyanide; acetic acid; In methanol;

DOI:10.1021/np970372u

Reference yield:

Agathene dicarboxylic acid-C15-methylester (14027-05-5,139628-86-7) → agathic acid (640-28-8) + labda-8(17),13(Z)-diene-15,19-dioic acid (640-28-8,17829-02-6,33123-07-8,37886-48-9,41988-89-0,138125-22-1)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

DOI:10.1021/np970372u

upstream raw materials:

Agathene dicarboxylic acid-C15-methylester

(E)-15-oxolabda-8⁽¹⁷⁾,13-diene-19-oic acid

isocupressic acid

Downstream raw materials:

dimethyl agathate

dihydroagathic acid

agathadiol

agathadiol

Refernces

• 1、 Garrossian, Massoud,Gardner, Dale R,Panter, Kip E,James, Lynn F. "Preparation of tetrahydroagathic acid: a serum metabolite of isocupressic acid, a cattle abortifacient in ponderosa pine.". . p. 2235 - 2240. Retrieved 2007/10/03.
• 2、 de Paiva Campello, Jayr,Marsaioli, Anita J.. "Terebenthifolic acid and bauerenone: New triterpenoid ketones from Schinus terebenthifolius". . p. 2300 - 2302. Retrieved 2007/10/13.