Basic information
- CAS
67-03-8- Standard SMILES
Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1.Cl.[Cl-]- InChIKey
DPJRMOMPQZCRJU-UHFFFAOYSA-M- Molecular formula
- C12H17N4OS.ClH.Cl
- Average molar mass
- 337.3 g/mol
- Monoisotopic mass
- 336.05783756
Overview
Thiamine hydrochloride is a hydrochloride obtained by combining thiamine chloride with one molar equivalent of hydrochloric acid. It has a role as an insect repellent. It is a vitamin B1 and a hydrochloride. It contains a thiamine(2+).
Names & identifiers
- Preferred name
- Thiamine Hydrochloride
- IUPAC
- 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;chloride;hydrochloride
- English name
- Thiamine hydrochloride
- Molecular formula
- C12H17N4OS.ClH.Cl
- Molecular weight
- 337.27
Names & synonyms
THIAMINE HYDROCHLORIDE67-03-8Thiamine HCLAneurine hydrochlorideVitamin B1 hydrochlorideClotiaminaEskaphenBetalin SThiamine chloride hydrochlorideThiamine dichlorideBevitineBenerva
Show more names
THIAMINEthdVITAMIN B1 HCLVB1 HCLVitamin B1 ThiamineVIT B1FEMA 3322200-641-8
Thiamin chlorideThiaminum hydrochloricumThiamin hydrochlorideBiamineBetabion hydrochlorideFEMA No. 3322Thiamin dichlorideThiaminium chloride hydrochloride
Database identifiers
- CAS
67-03-8- PubChem CID
- 6202
- DTXSID
DTXSID0040622- ChEMBL
CHEMBL1200941- ChEBI
CHEBI:49105- UNII
- M572600E5P
- EC Number
- 200-641-8
Properties
Computed structural properties
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 268
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Vitamins and Derivatives
CosmeticsSkin conditioning
Food AdditivesFLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
Soluble in water, propylene glycol; Insoluble in ether, benzene, hexane, chloroform
Slightly soluble (in ethanol)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physical Description
Solid with a mild thiazole odor; [Merck Index] White to light yellow crystalline powder; Hygroscopic; [Alfa Aesar MSDS]
Small white to yellowish crystals or crystalline powder; slight characteristic odour reminescent of thiazole
Physicochemical properties
- Melting point
- 250 °C · 250 °C (dec.)(lit.)
- Density
- 1.3766 · 1.3766 (rough estimate)
- bulk density
- 500 kg/m3 · 500kg/m3
- FLAVIS Number
- 16.027 · 16.027 | Thiamine hydrochloride
- refractive index
- 1.6 · 1.6000 (estimate)
- FEMA
- 3322 · 3322 | THIAMINE HYDROCHLORIDE
- Flash point
- 9 °C · 9°C
- storage temp.
- room temp
- solubility
- 2 O: · H2O: 0.1 g/mL at 20 °C, clear, colorless
- pka
- 4.8 · pKa 4.8 (Uncertain);9.0 (Uncertain)
- form
- Crystalline Powder
- color
- White to almost white
- PH
- 2.7 · 2.7-3.3
- Odor
- sour mild bitter
- Odor Type
- bland
- biological source
- synthetic (organic)
- Water Solubility
- 1 g/mL · 1 g/mL
- Sensitive
- Light Sensitive & Hygroscopic
- Merck
- 14 · 14,9295
- JECFA Number
- 1030 · 1030
- BRN
- 3851771 · 3851771
- BCS Class
- 3 · 3
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents, strong reducing agents.
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- SKIN CONDITIONINGFRAGRANCE
- InChI
- 1S/C12H17N4OS.2ClH/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;;/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);2*1H/q+1;;/p-1
- InChIKey
- DPJRMOMPQZCRJU-UHFFFAOYSA-M
- SMILES
- CC1=NC(N)=C(C[N+]2=CSC(CCO)=C2C)C=N1.Cl.[Cl-]
- LogP
- -3.93 · -3.93
- CAS DataBase Reference
- 67 · 67-03-8(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- THIAMINE HYDROCHLORIDE
- FDA 21 CFR
- 136.115 · 136.115; 137.165; 137.185;184.1875; 310.545; 582.5875
- SCOGS (Select Committee on GRAS Substances)
- Thiamine hydrochloride
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- thiamine
- FDA UNII
- 572600 E5P · M572600E5P
- NCI Drug Dictionary
- thiamine
- EPA Substance Registry System
- Thiamine hydrochloride (67-03-8)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 75 · NA.75
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi,T,F
- Risk Statements
- 36 · 36/37/38-39/23/24/25-23/24/25-11
- Safety Statements
- 22 · 22-24/25-37/39-26-36-45-36/37-16-7
- WGK Germany
- 1 · 1
- RTECS
- 7350000 · XI7350000
- F
- 3 · 3-8-10
- TSCA
- TSCA listed
- HS Code
- 29362200 · 29362200
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Eye Irrit. 2
- Toxicity
- 50 in · LD50 in mice (mg/kg): 89.2 i.v.; 8224 orally (Winter)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 66.2% (247 of 373) of all reports.
Warning
H319 (33.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 373 reports by companies from 12 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-, chloride, hydrochloride (1:1:1)
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 16-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/26096
Thiamine hydrochloride: Non hazardous
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryForms a hydrate on absorbing water from atmospheric humidity; [Merck Index] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS] See Thiamine.
Hazard Classes and CategoriesEye Irrit. 2 (33.2%)
Toxicology
Health EffectsThere are no reports available of adverse effects from consumption of excess thiamine by ingestion of food and supplements. [Wikipedia]
Exposure RoutesOral; parenteral (intravenous, intramuscular).
Absorbed mainly from duodenum, by both active and passive processes
Toxicity Summary
It is thought that the mechanism of action of thiamine on endothelial cells is related to a reduction in intracellular protein glycation by redirecting the glycolytic flux. Thiamine is mainly the transport form of the vitamin, while the active forms are phosphorylated thiamine derivatives. There are five known natural thiamine phosphate derivatives: thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and the recently discovered adenosine thiamine triphosphate (AThTP), and adenosine thiamine diphosphate. Each derivative has unique functions, however, most are involved as coenzymes.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Thiamine hydrochloride
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Toxicity DataLD50: 8224 mg/kg (Oral, Mouse) (A308)
LD50: 3710 mg/kg (Oral, Rat) (A308)
Safety data
- F
- 3-8-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- XI7350000
- hs_code
- 29362200
- Toxicity
- LD50 in mice (mg/kg): 89.2 i.v.; 8224 orally (Winter)
- risk_code
- 36/37/38-39/23/24/25-23/24/25-11
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,T,F
- safety_code
- 22-24/25-37/39-26-36-45-36/37-16-7
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHepatic
FDA Pharmacological Classification
METABOLIN
Increased Large Intestinal Motility [PE]; Cations, Divalent [CS]; Phosphate Chelating Activity [MoA]; Potassium Salt [EPC]; Stimulation Large Intestine Fluid/Electrolyte Secretion [PE]; Calcium [CS]; Potassium Compounds [CS]; Inhibition Small Intestine Fluid/Electrolyte Absorption [PE]; Amino Acids [CS]; Osmotic Laxative [EPC]; Magnesium Ion Exchange Activity [MoA]; Inhibition Large Intestine Fluid/Electrolyte Absorption [PE]; Increased Coagulation Factor Activity [PE]; Osmotic Activity [MoA]; Blood Coagulation Factor [EPC]; Phosphate Binder [EPC]; Calculi Dissolution Agent [EPC]; Amino Acid [EPC]
Uses & manufacturing
Uses
Used as a human and veterinary vitamin (enzyme cofactor); [Merck Index] An important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and PELLAGRA. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. [ChemIDplus] Used as a flavoring agent and nutritional supplement for foods; [FDA] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
For the treatment of thiamine and niacin deficiency states, Korsakov's alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis. Thiamine (hydrochloride) is a food additive used to add a brothy/meaty flavor to gravies or soups.
Household ProductsInformation on 5 consumer products that contain Thiamine hydrochloride in the following categories is provided:
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Cosmetics -> Skin conditioning
General Manufacturing InformationThiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-, chloride, hydrochloride (1:1:1): ACTIVE
Applications
DescriptionThiamine Hydrochloride is the hydrochloride salt form of thiamine (vitamin B1), a vitamin essential for aerobic metabolism, cell growth, transmission of nerve impulses and acetylcholine synthesis. Vitamin B1 helps prevent various health problems including heart damage.Thiamine hydrochloride is used to prevent and treat thiamine deficiency states, which may occur as a result of inadequate nutrition or intestinal malabsorption. It is also used for the treatment of Wernicke-Korsakoff syndrome, beriberi and thiamine deficiency related to chronic alcoholism. Thiamine hydrochloride is used as a food additive to add brothy/meaty flavor to gravies or soups. It is used also as a food supplement and flavoring ingredient with a bitter taste.
OccurrenceRice husks are reportedly the principal source of vitamin B1; in variable amounts it is a constituent of yeast, milk, green leaves, roots and tubers; it is also present in high concentration in seeds, and in lesser amount in different animal organs and muscles.
HistoryThiamine hydrochloride was the first water-soluble vitamin to be purified. In 1912, Cashmir Funk isolated thiamine from rice husks and coined the term ‘vitamine’ because it was required for life (‘vita’) and because thiamine contained nitrogen (‘amine’). Thiamine, formerly known as B1, is water soluble. Thiamine is a vital cofactor for enzymes and coenzymes of glycolysis, the Kreb’s cycle, the pentose phosphate pathway. Thiamine is also involved in the biosynthesis of the neurotransmitters acetylcholine and gamma-aminobutyric acid and in nerve propagation.
UsesThiamine is the water-soluble vitamin b1, required for normal digestion and functioning of nerve tissues and in the prevention of beriberi. It also acts as a coenzyme in the metabolism of carbohydrates. During processing, the higher and longer the heating period, the greater the loss. The loss is reduced in the presence of acid. Thiamine hydrochloride and thiamine mononitrate are two available forms. The mononitrate form is less hygroscopic and more stable than the hydrochloride form, making it suitable for use in beverage powders. It is used in enriched flour and is found as thiamine mononitrite in frozen egg substitute and crackers.
General DescriptionThiamine is a water-soluble vitamin of the B complex whose phosphate derivatives are involved in many cellular processes required for overall human health. Thiamine deficiency, often the result of impaired nutritional status associated with chronic diseases from alcoholism to HIV-AIDS, is monitored in patient whole blood samples by HPLC.
Preparation methods
PreparationBy linking the preformed thiazole and pyrimidine ring system.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 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]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
天津中信凯泰化工有限公司022-66880623 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎（中国）化学有限公司400-6106006 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [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]
上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
Beckmann-Kenko GmbH+49 4241 9308 88 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
台州市裕欣生物科技有限公司+86-0576--88902229 +86-13968687450
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
常州琬瑶生物科技有限公司0519-89185693 15312551983 · [email protected]
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司13636370518 · [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]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
上海贤鼎生物科技有限公司4009209199 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
潍坊沃腾进出口有限公司0536-2456718
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
Clearsynth Labs Limited+91-22-26355700 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [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400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
湖南华腾制药有限公司400-8592883 · [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]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
成都润泽本土化工有限公司13096311329 028-88469284 616445927 · [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]
Additional notes
DefinitionChEBI: Thiamine hydrochloride is a hydrochloride obtained by combining thiamine chloride with one molar equivalent of hydrochloric acid. It has a role as an insect repellent. It is a vitamin B1 and a hydrochloride. It contains a thiamine(2+).
Related reactions
42 records
Compound notes
Loading…