Xanthoxin

Base Information

Chemical Name:Xanthoxin
CAS No.:8066-07-7
Molecular Formula:C15H22O3
Molecular Weight:250.338
Hs Code.:
European Community (EC) Number:232-513-2
DSSTox Substance ID:DTXSID601035303
Metabolomics Workbench ID:54533
Wikidata:Q5933737
Wikipedia:Xanthoxin
Mol file:8066-07-7.mol

Synonyms:cis,trans-xanthoxin;trans,trans-5-(1',2'-epoxy-4'-hydroxy-2',6',6'- trimethyl-1'-cyclohexyl)-3-methylpentadienal;trans,trans-xanthoxin;xanthoxin;xanthoxin, (1R-(1alpha(2E,4E),4beta,6alpha))-isomer;xanthoxin, (1S-(1alpha(2E,4E),4alpha,6alpha))-isomer;xanthoxin, (1S-(1alpha(2Z,4E),4alpha,6alpha))-isomer

Suppliers and Price of Xanthoxin

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
Xanthoxin
50mg
$ 13390.00

Medical Isotopes, Inc.
Xanthoxin
50 mg
$ 13750.00

Medical Isotopes, Inc.
Xanthoxin
10 mg
$ 9750.00

Total 6 raw suppliers

Chemical Property of Xanthoxin

Chemical Property:

Boiling Point:371.1°Cat760mmHg
Flash Point:132.6°C
PSA：49.83000
Density:1.151g/cm³
LogP:2.39640
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:250.15689456
Heavy Atom Count:18
Complexity:422

Purity/Quality:

99% ^*data from raw suppliers

Xanthoxin ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(=CC=O)C=CC12C(CC(CC1(O2)C)O)(C)C
Isomeric SMILES:C/C(=C/C=O)/C=C/[C@]12[C@](O1)(C[C@H](CC2(C)C)O)C
Uses Xanthoxin is a growth inhibitor in plants.

Technology Process of Xanthoxin

There total 29 articles about Xanthoxin 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%

: 69350-47-6
(1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol

: 8066-07-7,28321-44-0
(1'S,2'R,4'S,2Z,4E)-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-dienal

Guidance literature:: With manganese(IV) oxide; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(01)80491-9

Reference yield:

: 130320-96-6
(-)-(1R,3S,6R)-6-ethynyl-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

: 8066-07-7,28321-44-0
(1'S,2'R,4'S,2Z,4E)-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-dienal

Guidance literature:: Multi-step reaction with 3 steps

1.1: nBu₃SnH / PdCl₂(PPh₃)2 / tetrahydrofuran / 0.17 h / 20 °C

1.2: 64 percent / CuI / PdCl₂(CH₃CN)2 / dimethylformamide / 20 h / 50 °C

2.1: 83 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / -25 °C

3.1: 92 percent / MnO₂ / diethyl ether / 5 h / 20 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; diethyl ether; 1.2: Stille reaction;
DOI:10.1246/cl.2002.1248

Reference yield:

: 214335-71-4
(-)-[(S)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-enyl]methanol

: 8066-07-7,28321-44-0
(1'S,2'R,4'S,2Z,4E)-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-dienal

Guidance literature:: Multi-step reaction with 7 steps

1.1: mCPBA / CH₂Cl₂ / 1 h / 20 °C

2.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 °C

3.1: nBuLi / tetrahydrofuran / 3 h / -30 °C

4.1: tBuOK / dimethylsulfoxide / 0.33 h / 20 °C

5.1: nBu₃SnH / PdCl₂(PPh₃)2 / tetrahydrofuran / 0.17 h / 20 °C

5.2: 64 percent / CuI / PdCl₂(CH₃CN)2 / dimethylformamide / 20 h / 50 °C

6.1: 83 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / -25 °C

7.1: 92 percent / MnO₂ / diethyl ether / 5 h / 20 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; potassium tert-butylate; tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; 2.1: Swern oxidation / 3.1: Wittig reaction / 5.2: Stille reaction;
DOI:10.1246/cl.2002.1248