Nicotianamine

Base Information

Chemical Name:Nicotianamine
CAS No.:34441-14-0
Molecular Formula:C₁₂H₂₁N₃O₆
Molecular Weight:303.315
Hs Code.:
UNII:2OGX6YHQ1F
DSSTox Substance ID:DTXSID8037677
Nikkaji Number:J18.352K
Wikipedia:Nicotianamine
Wikidata:Q11324211
Metabolomics Workbench ID:51016
ChEMBL ID:CHEMBL3581907
Mol file:34441-14-0.mol

Synonyms:N-(N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid;nicotianamine

Suppliers and Price of Nicotianamine

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
Nicotianamine
10mg
$ 1670.00

TRC
Nicotianamine
5mg
$ 965.00

Cayman Chemical
Nicotianamine ≥95%
1mg
$ 322.00

Cayman Chemical
Nicotianamine ≥95%
500μg
$ 190.00

AK Scientific
Nicotianamine
1mg
$ 502.00

Total 8 raw suppliers

Chemical Property of Nicotianamine

Chemical Property:

Vapor Pressure:0mmHg at 25°C
Melting Point:>220°C dec.
Boiling Point:633.3°Cat760mmHg
PKA:2.05±0.10(Predicted)
Flash Point:336.8°C
PSA：153.19000
Density:1.421g/cm³
LogP:-0.59070
Storage Temp.:Hygroscopic, -20?C Freezer, Under Inert Atmosphere
XLogP3:-8.2
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:10
Exact Mass:303.14303540
Heavy Atom Count:21
Complexity:403

Purity/Quality:

98%Min ^*data from raw suppliers

Nicotianamine ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1CN(C1C(=O)O)CCC(C(=O)O)NCCC(C(=O)O)N
Isomeric SMILES:C1CN([C@@H]1C(=O)O)CC[C@@H](C(=O)O)NCC[C@@H](C(=O)O)N
Uses Phytosiderophores are produced in higher plants as iron chelating amino acids that promote uptake of iron from soil.

Technology Process of Nicotianamine

There total 24 articles about Nicotianamine 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: 94.0%

: 159849-02-2
tert-butyl (2S,3'S,3S)-3'-(N-tert-butoxycarbonyl-3-tert-butoxycarbonyl-3-tert-butoxycarbonylaminopropylamino-3'-tert-butoxycarbonylpropyl)-2-azetidinecarboxylate

: 34441-14-0,54836-97-4,84412-98-6,111769-28-9
(2S:3'S:3''S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]-azetidine-2-carboxylic acid

Guidance literature:: With hydrogenchloride; DOWEX 50WX₄; methoxybenzene; 1.) THF, rt., 36 h; 2.) H₂O, 15percent aq. NH₃;
DOI:10.1016/S0040-4020(01)85520-4

Reference yield:

: 187796-30-1
(2S,3'S,3''S)-N-[3-(3-t-butoxycarbonyl-3-t-butoxycarbonylaminopropylamino)-3-t-butoxycarbonylpropyl]azetidine-2-carboxylic acid t-butyl ester

: 34441-14-0,54836-97-4,84412-98-6,111769-28-9
(2S:3'S:3''S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]-azetidine-2-carboxylic acid

Guidance literature:: With hydrogenchloride; methoxybenzene; In tetrahydrofuran; water; for 17h; Yield given; Ambient temperature;
DOI:10.3987/COM-96-S52

Reference yield:

: 201283-54-7
(2S,3'S,3''S)-N-[3-(3-t-butoxycarbonyl-3-t-butoxycarbonylaminopropanamido)-3-t-butoxycarbonylpropanoyl]azetidine-2-carboxylic acid t-butyl ester

: 34441-14-0,54836-97-4,84412-98-6,111769-28-9
(2S:3'S:3''S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]-azetidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 74 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / benzene / 5 h / 80 °C

2: 61 percent / Raney nickel / ethanol / 3 h / 50 °C

3: TFA

With Lawessons reagent; nickel; trifluoroacetic acid; In ethanol; benzene;
DOI:10.1016/S0040-4039(97)10496-8