基本情報
- 標準SMILES
Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1.Cl.[Cl-]- InChIKey
DPJRMOMPQZCRJU-UHFFFAOYSA-M- 分子式
- C12H17N4OS.ClH.Cl
- 平均分子量
- 337.3 g/mol
- 単同位体質量
- 336.05783756
概要
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+).
名称と識別子
- 優先名称
- Thiamine Hydrochloride
- IUPAC
- 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;chloride;hydrochloride
- 現地名
- 塩酸チアミン水和物
- 英語名
- Thiamine hydrochloride
- 分子式
- C12H17N4OS.ClH.Cl
- 分子量
- 337.27
名称と別名
名称をさらに表示
データベース識別子
- CAS
67-03-8- PubChem CID
- 6202
- DTXSID
DTXSID0040622- ChEMBL
CHEMBL1200941- ChEBI
CHEBI:49105- UNII
- M572600E5P
- EC Number
- 200-641-8
物性
構造計算による物性
- 極性表面積
- 104 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 6
- 回転可能結合数
- 4
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 268
実験および物理化学的性質
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
物理化学的性質
- 融点
- 250 °C · 250 °C (dec.)(lit.)
- 比重(密度)
- 1.3766 · 1.3766 (rough estimate)
- 屈折率
- 1.6 · 1.6000 (estimate)
- FEMA
- 3322 · 3322 | THIAMINE HYDROCHLORIDE
- 闪点
- 9 °C · 9°C
- 貯蔵温度
- room temp
- 溶解性
- 2 O: · H2O: 0.1g/mL at20℃ 無色透明
- 酸解離定数(Pka)
- 4.8 · pKa 4.8 (Uncertain);9.0 (Uncertain)
- 外見
- 結晶性粉末
- 色
- 白~ほぼ白
- PH
- 2.7 · 2.7-3.3
- 臭い (Odor)
- 酸味のあるマイルドな苦味
- においのタイプ
- 当たり障りのない
- 由来生物
- synthetic (organic)
- 水溶解度
- 1 g/mL · 1g/mL
- Merck
- 14 · 14,9295
- JECFA Number
- 1030 · 1030
- BRN
- 3851771 · 3851771
- BCS Class
- 3 · 3
- 安定性
- 安定。可燃性。強力な酸化剤、強力な還元剤とは相容れない。
- 主な用途
- フレーバーそして香料
- 化粧品成分の機能
- スキンコンディショニング香料
- 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 データベース
- 67 · 67-03-8(CAS DataBase Reference)
- EPAの化学物質情報
- Thiamine hydrochloride (67-03-8)
化学的性質
化学的特性Thiamine hydrochloride, also known as vitamin B1, is a white or almost white, crystalline powder or colorless crystals. It has an odor slightly reminiscent of thiazole and a bitter taste. Very soluble in water (1g dissolved in 1mL of water at 20℃), slightly soluble in ethanol, and insoluble in ether, benzene, chloroform, and acetone. The oxidation-reduction reaction can cause it to lose activity. When exposed to air, the vitamin rapidly absorbs about 4% of water.
安全と法規制
GHS分類
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.
危険有害性情報
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
毒性情報
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.
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
安全データ
- F
- 3-8-10
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- XI7350000
- 毒性
- LD50 in mice (mg/kg): 89.2 i.v.; 8224 orally (Winter)
- hs_code
- 29362200
- risk_code
- 36/37/38-39/23/24/25-23/24/25-11
- hazard_code
- Xi,T,F
- safety_code
- 22-24/25-37/39-26-36-45-36/37-16-7
- Hazard Classifications
- Eye Irrit. 2
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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]
用途と製造
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.
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
応用分野
解説ビタミンB1の別名,C12H18N4OCl2S(塩酸塩).抗脚気因子.胚芽,酵母などに含まれる.細胞中では主としてピロリン酸エステルとなり,さらにタンパク質などと結合して酵素成分となる.成人に1日約1 mg必要とされる.
用途ビタミン B1 化合物です。糖 質代謝に作用します。
説明Thiamine 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.
天然物の起源Rice 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.
来歴Thiamine 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.
使用Thiamine 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.
一般的な説明Thiamine 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.
調製方法
製造方法By linking the preformed thiazole and pyrimidine ring system.
純化方法The hydrochloride crystallises from 95% EtOH (solubility is ca 1%). The monohydrate is dehydrated at 100o in vacuo over H2SO4, but is hygroscopic and picks up one molecule of H2O readily. It can be sterilised at 100o if the pH of the solution is below 5.5. The nitrate has m 196-200o(dec) and is more stable than the hydrochloride. The picrolonate crystallises from H2O and is dimorphic, m 164-165o and 228-229o(dec). [Todd & Bergel J Chem Soc 364, 367 1937, J Am Chem Soc 58 1063, 1504 1936, 59 526 1937, Beilstein 27 IV 1766.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義本品は、複素環式化合物の塩酸塩であり、次の化学式で表される。
定義ChEBI: 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+).
関連反応
関連ノート
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