Ent-manool

Base Information

• Chemical Name: Ent-manool
• CAS No.: 596-85-0
• Molecular Formula: C20H34 O
• Molecular Weight: 290.489
• European Community (EC) Number: 637-366-1
• Nikkaji Number: J2.947.480J
• Wikidata: Q27146465
• Mol file: 596-85-0.mol

Synonyms:ent-manool;(3S)-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-ol;(13S)-ent-manool;CHEBI:76948;596-85-0;ent-labda-8(17),14-dien-13R-ol;Q27146465;(3S)-3-methyl-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl]pent-1-en-3-ol

Chemical Property of Ent-manool

Chemical Property:

• Vapor Pressure: 6.45E-07mmHg at 25°C
• Melting Point: 49-52 °C(lit.)
• Boiling Point: 368.2°Cat760mmHg
• PKA: 14.47±0.29(Predicted)
• Flash Point: 118.2°C
• PSA: 20.23000
• Density: 0.93g/cm³
• LogP: 5.50240
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 290.260965704
• Heavy Atom Count: 21
• Complexity: 422

Purity/Quality:

99.9% ^*data from raw suppliers

Manool(80%) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC(=C)C2CCC(C)(C=C)O)C)C
• Isomeric SMILES: C[C@@]12CCCC([C@H]1CCC(=C)[C@H]2CC[C@@](C)(C=C)O)(C)C
• Uses: Maintains anti-proliferative activity against human malignant cell strains.

Technology Process of Ent-manool

There total 25 articles about Ent-manool 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: 90.0%

8α-acetoxy-13R-hydroxy-labda-14-ene (22628-62-2) → manool (596-85-0)

Guidance literature:

With sodium hydrogencarbonate; In dimethyl sulfoxide; at 150 ℃; for 6h; regioselective reaction; Inert atmosphere;

DOI:10.3998/ark.5550190.0013.313

Reference yield: 82.0%

Toluene-4-sulfonic acid (2R,4aR,5S,8aR)-5-((S)-3-hydroxy-3-methyl-pent-4-enyl)-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester → (+)-manool (596-85-0,29461-42-5,41357-91-9,106631-38-3,1438-62-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

Reference yield: 40.0%

(E,E,E)-geranylgeranyl diphosphate (6699-20-3,13100-78-2,64732-91-8) → (+)-manool (596-85-0,29461-42-5,41357-91-9,106631-38-3,1438-62-6) + manool (596-85-0) + 8(17),13(E)-labdadien-15-ol (10395-43-4)

Guidance literature:

With DL-dithiothreitol; recombinant (+)-copalyl diphosphate synthase-GST fusion protein; recombinant Rv₃₃₇₈c enzyme from Mycobacterium tuberculosis; magnesium chloride; at 30 ℃; for 15h; pH=7.5; diastereoselective reaction; aq. buffer; Enzymatic reaction;

DOI:10.1039/c0ob00884b

upstream raw materials:

3-oxo-8⁽¹⁷⁾-labdadien-13R-ol

sclareol

8⁽¹⁷⁾-labdadien-3R,13R-diol

(E,E,E)-geranylgeranyl diphosphate

Downstream raw materials:

3α-acetoxy manool

(Z)-3-Methyl-5-((1S,4aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enal

(E)-3-Methyl-5-((1S,4aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enal

isopimara-8,15-diene

Refernces

• 1、 Rogachev, Victor,Loehl, Thorsten,Markert, Thomas,Metz, Peter. "A short and efficient synthesis of (+)-totarol". . p. 172 - 180. Retrieved 2013/09/24.
• 2、 Agarwal, S. G.,Thappa, R. K.,Dhar, K. L.. "Oxidation studies on 8(17),14-labdadien-3R,13R-diol: A major diterpene of Juniperus pseudosabina Hook". . p. 669 - 671. Retrieved 2007/10/03.