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塩酸チアミン水和物

Thiamine Hydrochloride

HCID 6202
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
67-03-8
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
336.0578378

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

THIAMINE HYDROCHLORIDE67-03-8Thiamine HCLAneurine hydrochlorideVitamin B1 hydrochlorideClotiaminaEskaphenThiamine chloride hydrochlorideBetalin SThiamine dichlorideBevitineBenerva
名称をさらに表示
塩酸チアミン水和物ビバチンビーワンベタボイン塩酸塩ビタミンB1チアミナールベアチンアクタミンロンベリンベタキシンベギオラン3-[(4-アミノ-2-メチルピリミジン-5-イル)メチル]-5-(2-ヒドロキシエチル)-4-メチルチアゾール-3-イウム·クロリド·塩酸塩3-[(4-アミノ-2-メチル-5-ピリミジニル)メチル]-5-(2-ヒドロキシエチル)-4-メチルチアゾール-3-イウム·クロリド·塩酸塩塩酸アノイリンメタポリンメタボリンムツタミンアノイリン塩酸塩ベタリンS塩酸チアミンTHIAMINEthdVITAMIN B1 HCLVB1 HCLVitamin B1 ThiamineVIT B1FEMA 3322200-641-8
Thiamin chlorideThiaminum hydrochloricumThiamin hydrochlorideBiamineBetabion hydrochlorideFEMA No. 3322Thiamin dichlorideThiaminium chloride hydrochloride

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補完中

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

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 · 2 件

Soluble in water, propylene glycol; Insoluble in ether, benzene, hexane, chloroform

Slightly soluble (in ethanol)

Human Drugs · 2 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical Description · 2 件

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 · 1 件

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

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

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 · 4 件

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)

REACH registered substance: Thiamine hydrochloride (EC: 200-641-8)

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%)

毒性情報

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 · 1 件

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 · 6 件

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)

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

Metabolism/MetabolitesHepatic
FDA Pharmacological Classification · 2 件

METABOLIN

Phosphate Binder [EPC]; Increased Large Intestinal Motility [PE]; Blood Coagulation Factor [EPC]; Potassium Salt [EPC]; Amino Acid [EPC]; Stimulation Large Intestine Fluid/Electrolyte Secretion [PE]; Phosphate Chelating Activity [MoA]; Calcium [CS]; Cations, Divalent [CS]; Calculi Dissolution Agent [EPC]; Increased Coagulation Factor Activity [PE]; Osmotic Activity [MoA]; Amino Acids [CS]; Osmotic Laxative [EPC]; Potassium Compounds [CS]; Inhibition Large Intestine Fluid/Electrolyte Absorption [PE]; Magnesium Ion Exchange Activity [MoA]; Inhibition Small Intestine Fluid/Electrolyte Absorption [PE]

用途と製造

Uses · 2 件

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 · 5 件

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
応用分野 · 7 件

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 · 2 件

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

アセトアミジン塩酸塩プロピオナートキノリンチアミン硝酸塩硝酸アンモニウムN,N-ジメチルカルバミド酸6-メチル-2-プロピルピリミジン-4-イル二硫化炭素3-メトキシプロピオニトリルThiamine Impurity 21水和物

下流製品

チアミン硝酸塩2-Pentanone, 5-hydroxy-3-mercapto- (6CI,7CI,9CI)チアミン
補足説明 · 2 件

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

42 件
反応記録を作成
HRID 262936 の反応式
HRID 262936反応物としてuspto-grants-1979_05
HRID 268589 の反応式
HRID 268589反応物としてuspto-grants-2008_11
HRID 418976 の反応式
HRID 418976反応物としてuspto-grants-2012_01
HRID 476589 の反応式
HRID 476589反応物としてuspto-grants-1989_12
HRID 482970 の反応式
HRID 482970反応物としてuspto-grants-1986_03
HRID 487044 の反応式
HRID 487044反応物としてuspto-grants-1994_03
HRID 487045 の反応式
HRID 487045反応物としてuspto-grants-1994_03
HRID 487046 の反応式
HRID 487046反応物としてuspto-grants-1994_03
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