Basic information
- Standard SMILES
OCC(O)CS- InChIKey
PJUIMOJAAPLTRJ-UHFFFAOYSA-N- Molecular formula
- C3H8O2S
- Average molar mass
- 108.16 g/mol
- Monoisotopic mass
- 108.0245005
Overview
Monothioglycerol is a thiol that is glycerol in which one of the primary hydroxy groups is replaced by a thiol group. It has a role as a reducing agent and a vulnerary. It is a member of propane-1,2-diols and a thiol.
Names & identifiers
- Preferred name
- Thioglycerol
- IUPAC
- 3-sulfanylpropane-1,2-diol
- English name
- 3-Mercapto-1,2-propanediol
- Molecular formula
- C3H8O2S
- Molecular weight
- 108.16
Names & synonyms
3-Mercapto-1,2-propanediol1-Thioglycerol96-27-5MonothioglycerolTHIOGLYCEROLThioglycerinThiovanolalpha-ThioglycerolThioglycerineGlycerol-1-thiol1-Mercaptoglycerol1-Monothioglycerol
Show more names
3-Mercaptopropane-1,2-diolA-MONOTHIOGLYCEROL
1,2-Propanediol, 3-mercapto-Monothioglycerin2,3-Dihydroxypropanethiol1-Mercapto-2,3-propanediolalpha-ThiolglycerolGlycerol, 1-thio-alpha-Monothioglycerol1-Thio-2,3-propanediol
Database identifiers
- CAS
96-27-5- PubChem CID
- 7291
- DTXSID
DTXSID5046512- ChEMBL
CHEMBL1398948- ChEBI
CHEBI:74537- UNII
- AAO1P0WSXJ
- EC Number
- 202-495-0
- Nikkaji
- J3.966G
Properties
Computed structural properties
- XLogP
- -0.8
- Topological polar surface area
- 41.5 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 32
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Sulfur Compounds (Alcohols)
CosmeticsHair waving or straightening; Depilatory; Keratolytic; Reducing
SpringerMaterials PropertiesOptical coefficient
OdorSLIGHT SULFIDIC
Density1.295
Color/Form
YELLOWISH, VERY VISCOUS LIQUID
COLORLESS OR PALE YELLOW
Solubility
SLIGHTLY SOL IN WATER; MISCIBLE WITH ALCOHOL; INSOL IN ETHER
VERY SOL IN ACETONE; SLIGHTLY SOL IN BENZENE
Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Boiling Point118 °C @ 5 MM HG
DecompositionWHEN HEATED TO DECOMP, EMITS HIGHLY TOXIC FUMES OF /SULFUR OXIDES/
Refractive IndexINDEX OF REFRACTION BETWEEN 1.521 & 1.526; PH (1 IN 10 SOLN) BETWEEN 3.5 & 7
Physical Description
Liquid
Water-white liquid; Soluble in water; [Hawley] Yellowish hygroscopic liquid; Slightly soluble in water; [Merck Index] Colorless viscous liquid with a stench; Slightly soluble in water; [MSDSonline]
Physicochemical properties
- Melting point
- 25 °C · <25 °C
- Boiling point
- 118 °C5 · 118 °C5 mm Hg(lit.)
- Density
- 1.25 g/mL · 1.25 g/mL at 25 °C(lit.)
- vapor pressure
- 1 hPa · <1 hPa (20 °C)
- refractive index
- 20 · n20/D 1.527(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 1 mL/mL · absolute ethanol: 1 mL/mL
- form
- liquid
- pka
- 1 · pK1:9.43 (25°C,μ=0.5)
- color
- Clear colorless to yellow
- Odor
- Stench odour
- PH
- 3.5 · 3.5-7.0
- biological source
- synthetic (organic)
- Water Solubility
- slightly soluble
- Sensitive
- Air Sensitive & Hygroscopic
- Merck
- 14 · 14,9335
- BRN
- 1732046 · 1732046
- Stability
- Air Sensitive, Hygroscopic
- Cosmetics Ingredients Functions
- DEPILATORYKERATOLYTICHAIR WAVING OR STRAIGHTENINGREDUCING
- InChI
- 1S/C3H8O2S/c4-1-3(5)2-6/h3-6H,1-2H2
- InChIKey
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N
- SMILES
- OCC(O)CS
- LogP
- -0.84 at · -0.84 at 20℃
- CAS DataBase Reference
- 96 · 96-27-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 P0WSXJ · AAO1P0WSXJ
- NIST Chemistry Reference
- Monothioglycerol(96-27-5)
- EPA Substance Registry System
- 1 · 1,2-Propanediol, 3-mercapto- (96-27-5)
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 75 · NA.75
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 302 · H302-H311-H315-H317
- Precautionary statements
- 280 · P280-P301+P312+P330-P302+P352+P312
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,Xi
- Risk Statements
- 21 · 21/22-36/37/38
- Safety Statements
- 26 · 26-36-23
- RIDADR
- 2810 · UN 2810 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 8140000 · TY8140000
- F
- 3 · 3-9-10-13-23
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29309070 · 29309070
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 4 OralSkin Irrit. 2Skin Sens. 1B
- Hazardous Substances Data
- 96 · 96-27-5(Hazardous Substances Data)
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (93.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P262, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 362 reports by companies from 24 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1,2-Propanediol, 3-mercapto-
1,2-Propanediol, 3-mercapto- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Propanediol, 3-mercapto- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 16-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24546
Monothioglycerol: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Fire PotentialFIRE HAZARD: MODERATE. ...CAN REACT WITH OXIDIZING MATERIALS.
Hazards SummaryAn irritant; Effects in high-dose animal studies include lacrimation and convulsions; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (93.9%)
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Safety data
- F
- 3-9-10-13-23
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- TY8140000
- ridadr
- UN 2810 6.1/PG 3
- hs_code
- 29309070
- risk_code
- 21/22-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn,Xi
- safety_code
- 26-36-23
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H302-H311-H315-H317
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 4 OralSkin Irrit. 2Skin Sens. 1B
- Precautionary statements
- P280-P301+P312+P330-P302+P352+P312
- Hazardous Substances Data
- 96-27-5(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as a preservative (pharmaceuticals), reducing agent , and polymer stabilizer; [HSDB] Used as a preservative (antioxidant), analytical reagent, and research chemical; [Merck Index]
IN WOUND HEALING; VET: TO PROMOTE WOUND HEALING (SOLN 1:5000)
PHARMACEUTIC AID (PRESERVATIVE)
REDUCING AGENT FOR CYSTINE MOLECULE IN HUMAN HAIR & WOOL; FOR STABILIZATION OF ACRYLONITRILE POLYMERS
U.S. Production2023: 51,570 lb
Consumer UsesStabilizing agent
Industry UsesPreservative
Methods of ManufacturingPREPD BY HEATING GLYCEROL-ALPHA-MONOCHLOROHYDRIN WITH KHS IN ALCOHOLIC SOLUTION. SUTTON, J AM MED ASSOC 104, 2168 (1935).
Use ClassificationCosmetics -> Hair waving or straightening; Depilatory; Keratolytic; Reducing
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
1,2-Propanediol, 3-mercapto-: ACTIVE
...MEAT FLAVORS WERE OBTAINED...BY REACTION...WITH HYDROGEN SULFIDE RELEASING AGENTS UNDER PRESSURE. ... HYDROGEN SULFIDE RELEASING AGENTS MENTIONED INCL... 3-MERCAPTO-1,2-PROPANEDIOL... PRACTICALLY ALL THESE COMPD ARE POWERFUL FLAVOR COMPD THEMSELVES.
Applications
Description1-Thioglycerol is a reagent used in fluorescence, spectroscopy, and microbiology techniques. Varying the concentration of 1-thioglycerol in the preparation of CdSe/CdS core-shell ultrasmall quantum dots (CS-USQDs) allows a precise way to control the size of the shell, with shell size increasing with increased concentration. It is used as a capping agent in the synthesis of nanocrystals analyzed via Raman and UV/Vis spectroscopy. Biologically, 1-thioglycerol stimulates porphyrin synthesis and increases glutamyl-tRNA reductase activity in E. coli grown in an aerobic environment. It was previously a component in hair permanents used to produce waves or curls.
UsesIt generally used as a size-regulating capping agent for nanocrystals. 1-Thioglycerol is also used in bacteriology experiments to induce the synthesis of porphyrin compounds in aerobically growing Escherichia coli. Also used to study the pH-sensitive photoluminescence of aqueous thiol-capped CdTe nanocrystals. 1-Thioglycerol is used to develop and test thiol functionalized copolymers. 1-Thioglycerol is used as a post-modification agent in the generation of non-standard peptide foldamers.Potential substitute for 2-mercaptoethanol, probe for the study of lymphocyte activation.
Uses3-Mercapto-1,2-propanediol can be used as antioxidant preservative; reagent in analytical chemistry, cell culture research. Matrix substrate in fast atom bombardment mass spectrometry.
Uses3-Mercapto-1,2-propanediol has been used in a study to assess the manipulation of aqueous growth of CdTe nanocrystals. It has also been used in a study that investigated the effect of surface attachment on ligand binding
General Description1-Thioglycerol stimulates the synthesis of porphyrin in aerobically growing Escherichia coli. It is an inhibitor of glycerol kinase activity in vitro and in situ.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
洛辅医药科技(嘉兴)有限公司17621761986
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
上海泰矶林实业有限公司02150630626 17717886015 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
上海弘顺生物科技有限公司15901914505 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
阿法埃莎（中国）化学有限公司400-6106006 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
北京绿百草科技发展有限公司010-61136123 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技（中国）有限公司800-810-5118 · [email protected]
北京伊诺凯科技有限公司400-810-7969 010-59572699 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
石家庄鲲翔达科技有限公司0311-89683399 15373948595
重庆卡兰医药有限公司023-62879767 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
上海毕得医药科技股份有限公司400-164-7117 18317119277 · [email protected]
重庆星灿医药科技有限公司13594048950 19923294409 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
潍坊市前进精细化工有限公司18753684562 · [email protected]
北京诺其雅盛生物科技有限公司4000-819-385 010-62329685 13718666987
Additional notes
DefinitionChEBI: A thiol that is glycerol in which one of the primary hydroxy groups is replaced by a thiol group.
Related reactions
51 records
Linked notes
Loading…