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333131

Sigma-Aldrich

N,N′-Bis(2-aminoethyl)-1,3-propanediamine

97%

Synonym(s):

1,3-Bis(2-aminoethylamino)propane, 1,4,8,11-Tetraazaundecane, 1,9-Diamino-3,7-diazanonane, 3,7-Diaza-1,9-diaminononane, 3,7-Diazanonane-1,9-diamine, Ethylene(trimethylene)ethylenetetramine, N,N′-Bis(2-aminoethyl)propane-1,3-diamine, N1,N3-Bis(2-aminoethyl)-1,3-propanediamine, Triethylene 2,3,2 tetramine

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About This Item

Linear Formula:
H2NCH2CH2NH(CH2)3NHCH2CH2NH2
CAS Number:
4741-99-5
Molecular Weight:
160.26
Beilstein:
1742732
EC Number:
225-254-1
MDL number:
MFCD00008174
UNSPSC Code:
12352100
PubChem Substance ID:
24860105
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.494 (lit.)

bp

142-145 °C/8 mmHg (lit.)

density

0.96 g/mL at 25 °C (lit.)

SMILES string

NCCNCCCNCCN

InChI

1S/C7H20N4/c8-2-6-10-4-1-5-11-7-3-9/h10-11H,1-9H2

InChI key

UWMHHZFHBCYGCV-UHFFFAOYSA-N

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General description

N,N′-Bis(2-aminoethyl)-1,3-propanediamine is a high affinity Cu(II) chelator. It inhibits mitochondrial cytochrome c oxidase by causing cellular Cu deficiency in a human promyelocytic leukemia cell line (HL-60).

Application

N,N′-Bis(2-aminoethyl)-1,3-propanediamine was used to study the regulation of gene that encodes the periplasmic superoxide dismutase of Escherichia coli in response to copper.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Changyong Cheng et al.
Journal of medical microbiology, 62(Pt 6), 813-821 (2013-03-23)
The foodborne pathogen Listeria monocytogenes is able to colonize the human and animal intestinal tracts and subsequently crosses the intestinal barrier, causing systemic infection. For successful establishment of infection, L. monocytogenes must survive and adapt to the low pH environment
Laura J Raymond et al.
Experimental biology and medicine (Maywood, N.J.), 229(9), 885-894 (2004-09-25)
Cytochrome c oxidase (CCO) is the Cu-dependent, terminal respiratory complex of the mitochondrial electron transport chain. Inhibition of CCO can promote oxidative stress by increasing mitochondrial production of reactive oxygen species (ROS). Because mitochondria have an important role in apoptosis
Zhouxi Wang et al.
BMC bioinformatics, 14 Suppl 3, S13-S13 (2013-03-27)
The prediction of biochemical function from the 3D structure of a protein has proved to be much more difficult than was originally foreseen. A reliable method to test the likelihood of putative annotations and to predict function from structure would
A S Gort et al.
Molecular microbiology, 32(1), 179-191 (1999-04-27)
The discovery of superoxide dismutase (CuZnSOD) within the periplasms of several Gram-negative pathogens suggested that this enzyme evolved to protect cells from exogenous sources of superoxide, such as the oxidative burst of phagocytes. However, its presence in some non-pathogenic bacteria
Gottfried K Schroeder et al.
Biochemistry, 52(24), 4204-4216 (2013-05-23)
cis-3-Chloroacrylic acid dehalogenase (cis-CaaD) from Pseudomonas pavonaceae 170 and a homologue from Corynebacterium glutamicum designated Cg10062 are 34% identical in sequence (54% similar). The former catalyzes a key step in a bacterial catabolic pathway for the nematocide 1,3-dichloropropene, whereas the
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