Berteroin

Base Information

• Chemical Name: Berteroin
• CAS No.: 4430-42-6
• Molecular Formula: C₇H₁₃NS₂
• Molecular Weight: 175.319
• Hs Code.: 2930909090
• UNII: 0L0K74BW6T
• DSSTox Substance ID: DTXSID00196119
• Nikkaji Number: J634.913G
• Wikidata: Q27236919
• Pharos Ligand ID: FSYWG3L2HCGD
• Metabolomics Workbench ID: 44966
• ChEMBL ID: CHEMBL3593947
• Mol file: 4430-42-6.mol

Synonyms:5-methylthiopentyl isothiocyanate;berteroin

Chemical Property of Berteroin

Chemical Property:

• Vapor Pressure: 0.0132mmHg at 25°C
• Melting Point: 155～156℃
• Boiling Point: 267.7°Cat760mmHg
• Flash Point: 115.7°C
• PSA: 69.75000
• Density: 1.01g/cm³
• LogP: 2.62250
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 175.04894177
• Heavy Atom Count: 10
• Complexity: 108

Purity/Quality:

98% ^*data from raw suppliers

Berteroin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCCCCN=C=S
• Description: Berteroin is a sulforaphane analog found in cruciferous vegetables including Chinese cabbage, rucola salad leaves, and mustard oil. At 1.7 μM, it has been shown to double the phase II enzyme quinone reductase activity in mouse hepatoma cells. Berteroin exerts anti-inflammatory activity in LPS-stimulated RAW 264.7 macrophages, inhibiting degradation of IκBα, as well as NF-κB p65 translocation to the nucleus and DNA binding activity. It also suppresses IRAK degradation and phosphorylation of TAK1, p38 MAPK, ERK1/2, and Akt.
• Uses: Berteroin is a compound with high odor potency occurring in horseradish ( Armoracia rusticana)

Technology Process of Berteroin

There total 7 articles about Berteroin 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: 75.0%

thiophosgene (463-71-8) + 5-methylthiopentylamine (55021-78-8) → berteroin (4430-42-6)

Guidance literature:

With sodium hydroxide; In chloroform; at 20 ℃; for 1h;

DOI:10.1021/jf1003573

Reference yield: 64.0%

methylthiol (74-93-1) + 4-pentenyl isothiocyanate (18060-79-2) → berteroin (4430-42-6)

Guidance literature:

With tert.-butylhydroperoxide; In methanol; at 20 ℃; for 9h;

DOI:10.1021/acs.jnatprod.5b00272

Reference yield:

5-bromopentan-1-nitrile (5414-21-1) → berteroin (4430-42-6)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol

2: lithium alanate; diethyl ether

3: chloroform; aqueous sodium hydrogencarbonate

With methanol; lithium aluminium tetrahydride; diethyl ether; chloroform; sodium hydrogencarbonate;

upstream raw materials:

thiophosgene

5-methylthiopentylamine

2-<5-(methylthio)pentyl>-1H-isoindol-1,3(2H)-dione

5-bromopentan-1-nitrile

Downstream raw materials:

alyssin

(R)-1-isothiocyanato-5-(methylsulfinyl)pentane

Refernces

• 1、 Moon, Joon-Kwan,Kim, Jun-Ran,Ahn, Young-Joon,Shibamoto, Takayuki. "Analysis and anti- helicobacter activity of sulforaphane and related compounds present in Broccoli (Brassica oleracea L.) sprouts". experimental part. p. 6672 - 6677. Retrieved 2011/08/06.