96-27-5 Usage
Description
3-Mercapto-1,2-propanediol, also known as 1-thioglycerol, is a colorless to pale-yellow colored, viscous, hygroscopic liquid with a slight odor of sulfide. It is a thiol that is glycerol in which one of the primary hydroxy groups is replaced by a thiol group. It is used as a reagent in various fields, including fluorescence, spectroscopy, and microbiology techniques.
Uses
Used in Nanocrystal Synthesis:
3-Mercapto-1,2-propanediol is used as a size-regulating capping agent for nanocrystals, allowing precise control of the size of the shell in CdSe/CdS core-shell ultrasmall quantum dots (CS-USQDs). It is also used in the synthesis of nanocrystals analyzed via Raman and UV/Vis spectroscopy.
Used in Analytical Chemistry and Cell Culture Research:
3-Mercapto-1,2-propanediol is used as an antioxidant preservative and reagent in analytical chemistry and cell culture research. It serves as a matrix substrate in fast atom bombardment mass spectrometry.
Used in Bacteriology Experiments:
In bacteriology, 3-Mercapto-1,2-propanediol is used to induce the synthesis of porphyrin compounds in aerobically growing Escherichia coli. It also stimulates porphyrin synthesis and increases glutamyl-tRNA reductase activity in E. coli grown in an aerobic environment.
Used in the Study of pH-Sensitive Photoluminescence:
3-Mercapto-1,2-propanediol is used to study the pH-sensitive photoluminescence of aqueous thiol-capped CdTe nanocrystals.
Used in the Development and Testing of Thiol Functionalized Copolymers:
3-Mercapto-1,2-propanediol is used in the development and testing of thiol functionalized copolymers.
Used as a Post-Modification Agent:
3-Mercapto-1,2-propanediol is used as a post-modification agent in the generation of non-standard peptide foldamers.
Used as a Potential Substitute for 2-Mercapoethanol:
3-Mercapto-1,2-propanediol can be used as a potential substitute for 2-mercaptoethanol, serving as a probe for the study of lymphocyte activation.
Used in the Manipulation of Aqueous Growth of CdTe Nanocrystals:
3-Mercapto-1,2-propanediol has been used in a study to assess the manipulation of aqueous growth of CdTe nanocrystals.
Used in the Investigation of Surface Attachment on Ligand Binding:
3-Mercapto-1,2-propanediol has been used in a study that investigated the effect of surface attachment on ligand binding.
Production Methods
Monothioglycerol is prepared by heating an ethanolic solution of 3-
chloro-1,2-propanediol with potassium bisulfide.
Pharmaceutical Applications
Monothioglycerol is used as an antioxidant in pharmaceutical
formulations, mainly in parenteral preparations.Monothioglycerol
is reported to have some antimicrobial activity.It is also
widely used in cosmetic formulations such as depilating agents.
Therapeutically, monothioglycerol has been used in a 0.02%
w/w aqueous solution to stimulate wound healing, and as a 0.1%
w/w jelly in atrophic rhinitis.
Safety Profile
Poison by
intraperitoneal and intravenous routes.
Experimental reproductive effects. Mutation
data reported. Flammable when exposed to
heat or flame; can react with oxidizing
materials. When heated to decomposition it
emits hghly toxic fumes of SOx.
Safety
Monothioglycerol is generally regarded as a relatively nontoxic and
nonirritant material at the concentrations used as a pharmaceutical
excipient. It is used in topical and injectable preparations.
Undiluted monothioglycerol is considered a poison by the IP and
IV routes; it has also been reported to be mutagenic.
LD50 (cat, IV): 0.22 g/kg
LD50 (mouse, IP): 0.34 g/kg
LD50 (rabbit, IV): 0.25 g/kg
LD50 (rat, IP): 0.39 g/kg
storage
Monothioglycerol is unstable in alkaline solutions. Monothioglycerol
should be stored in a well-closed container in a cool, dry place.
Incompatibilities
Monothioglycerol can react with oxidizing materials.
Regulatory Status
Included in the FDA Inactive Ingredients Database (IM, IV and
other injections). Included in the Canadian List of Acceptable Nonmedicinal
Ingredients.
Check Digit Verification of cas no
The CAS Registry Mumber 96-27-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 96-27:
(4*9)+(3*6)+(2*2)+(1*7)=65
65 % 10 = 5
So 96-27-5 is a valid CAS Registry Number.
InChI:InChI=1/C3H8O2S/c4-1-3(5)2-6/h3-6H,1-2H2/t3-/m0/s1
96-27-5Relevant articles and documents
Template effects of vesicles in dynamic covalent chemistry
Bravin, Carlo,Hunter, Christopher A.
, p. 9122 - 9125 (2020/09/17)
Vesicle lipid bilayers have been employed as templates to modulate the product distribution in a dynamic covalent library of Michael adducts formed by mixing a Michael acceptor with thiols. In methanol solution, all possible Michael adducts were obtained in similar amounts. Addition of vesicles to the dynamic covalent library led to the formation of a single major product. The equilibrium constants for formation of the Michael adducts are similar for all of the thiols used in this experiment, and the effect of the vesicles on the composition of the library is attributed to the differential partitioning of the library members between the lipid bilayer and the aqueous solution. The results provide a quantitative approach for exploiting dynamic covalent chemistry within lipid bilayers. This journal is
Keratinocyte growth factor-2 formulations
-
, (2008/06/13)
The invention is directed to liquid and lyophilized forms of Keratinocyte Growth Factor-2 (KGF-2) and derivatives thereof. This invention further relates to the formulation of KGF-2 for therapeutic use, for example, to promote or accelerate wound healing.
Reaction of ascorbic acid with S-nitrosothiols: Clear evidence for two distinct reaction pathways
Holmes, Anthony J.,Williams, D. Lyn H.
, p. 1639 - 1644 (2007/10/03)
Ascorbate reacts with S-nitrosothiols generally, in the pH range 3-13 by way of two distinct pathways, (a) at low [ascorbate], typically below ～1 × 10-4 mol dm-3 which leads to the formation of NO and the disulfide, and (b) at higher [ascorbate] when the products are the thiol and NO. Reaction (a) is Cu2+-dependent, and is completely cut out in the presence of EDTA, whereas reaction (b) is totally independent of [Cu2+] and takes place readily whether EDTA is present or not. For S-nitrosoglutathione (GSNO) the two reactions can be made quite separate, although for some reactants the two reactions overlap. In reaction (a), ascorbate acts as a reducing agent, generating Cu+ from Cu2+, which in turn reacts with RSNO forming initially NO, Cu2+ and RS-. The latter can then play the role of reducing agent for Cu2+, leading to disulfide formation. Ascorbate will initiate reaction when the free thiolate has initially been reduced to a very low level by the synthesis of RSNO from a large excess of nitrous acid over the thiol. Reaction (b) is interpreted in terms of nucleophilic attack by ascorbate at the nitroso-nitrogen atom, leading to thiol and O-nitrosoascorbate which breaks up, by a free-radical pathway, to give dehydroascorbic acid and NO. A similar pathway is the accepted mechanism in the literature for the nitrosation of ascorbate by nitrous acid and alkyl nitrites. The rate constant for the Cu2+-independent pathway increases sharply with pH and analysis of the variation of the rate constant with pH identifies a reaction pathway via both the mono- and di-anion forms of ascorbate, with the latter being the more reactive. As expected the entropy of activation is large and negative. Some aspects of structure-reactivity trends are discussed.
