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64046

Sigma-Aldrich

2,3-Dimercapto-1-propanol

≥98% (iodometric)

Synonym(s):

BAL, British anti-Lewisite, DMP, Dimercaprol, Dithioglycerol

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About This Item

Linear Formula:
HOCH2CH(SH)CH2SH
CAS Number:
59-52-9
Molecular Weight:
124.23
Beilstein:
1732058
EC Number:
200-433-7
MDL number:
MFCD00004864
UNSPSC Code:
12352100
PubChem Substance ID:
57651969
NACRES:
NA.22

Assay

≥98% (iodometric)

refractive index

n20/D 1.572-1.574
n20/D 1.573 (lit.)

bp

120 °C/15 mmHg (lit.)

density

1.239 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

OCC(S)CS

InChI

1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2

InChI key

WQABCVAJNWAXTE-UHFFFAOYSA-N

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General description

Dimercapto-1-propanol acts as a chelating agent and forms stable complexes with certain heavy metals, including arsenic, mercury, and lead.

Application

2,3-Dimercapto-1-propanol has been used in synthesizing novel (2-substituted phenyl-1,3-dithiolan-4-yl) methanol (PDTM) derivatives, which are potent tyrosinase inhibitors. It can also be considered for developing new drugs against AIDS due to its ability to inhibit HIV-1 tat activity.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

233.6 °F - closed cup

Flash Point(C)

112 °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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S Kubota et al.
AIDS research and human retroviruses, 6(7), 919-927 (1990-07-01)
We have examined the effect of 2,3 dimercapto-1-propanol (DMP), which is known as an anti-heavy metal-poisoning drug, against human immunodeficiency virus type 1 (HIV-1). We demonstrate that DMP inhibited transactivation directed by tat protein, which is a metal containing transcriptional
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American journal of physiology. Lung cellular and molecular physiology, 307(12), L948-L958 (2014-10-12)
Bronchopulmonary dysplasia (BPD) is the chronic lung disease of prematurity that affects very preterm infants. Although advances in perinatal care have enabled the survival of infants born as early as 23-24 wk of gestation, the challenge of promoting lung growth
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Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 60(5), 713-720 (2014-11-22)
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Do Hyun Kim et al.
Drug design, development and therapy, 11, 827-836 (2017-03-30)
The authors designed and synthesized 17 (2-substituted phenyl-1,3-dithiolan-4-yl) methanol (PDTM) derivatives to find a new chemical scaffold, showing excellent tyrosinase-inhibitory activity. Their tyrosinase-inhibitory activities were evaluated against mushroom tyrosinase at 50 μM, and five of the PDTM derivatives (PDTM3, PDTM7-PDTM9
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