(2S)-N,N,N-トリメチル-2-ヒドロキシ-3-カルボキシラト-1-プロパンアミニウム

D-Carnitine

HCID 2724480

基本情報

CAS
541-14-0
標準SMILES
C[N+](C)(C)C[C@@H](O)CC(=O)[O-]
InChIKey
PHIQHXFUZVPYII-LURJTMIESA-N
分子式
C7H15NO3
平均分子量
161.2 g/mol

概要

(S)-carnitine is the (S)-enantiomer of carnitine. It is a conjugate base of a (S)-carnitinium. It is an enantiomer of a (R)-carnitine.

名称と識別子

優先名称
D-Carnitine
IUPAC
(3S)-3-hydroxy-4-(trimethylazaniumyl)butanoate
現地名
(2S)-N,N,N-トリメチル-2-ヒドロキシ-3-カルボキシラト-1-プロパンアミニウム
英語名
D(+)-Carnitine
分子式
C7H15NO3
分子量
161.2

名称と別名

D-carnitine541-14-0D-(+)-carnitine(+)-Carnitine(S)-carnitine(3S)-3-hydroxy-4-(trimethylazaniumyl)butanoateCarnitine, (+)-UNII-U9VY0ZOK7AU9VY0ZOK7ACARNITINE, D-(3S)-3-hydroxy-4-(trimethylammonio)butanoate(+)-D-CARNITINE
名称をさらに表示
(S)-カルニチン(S)-N,N,N-トリメチル-3-カルボキシラト-2-ヒドロキシ-1-プロパンアミニウムD-カルニチン[(2S)-2-ヒドロキシ-3-カルボキシラトプロピル]トリメチルアミニウムD-(+)カルニチンD(+)-カルニチン(+)-(3-カルボキシ-2-ヒドロキシプロピル)トリメチルアンモニウム分子内塩D-ビタミンBT[S,(+)]-3-ヒドロキシ-4-(トリメチルアミニオ)ブチラート[S,(+)]-3-カルボキシラト-2-ヒドロキシ-N,N,N-トリメチルプロパン-1-アミニウム(2S)-N,N,N-トリメチル-2-ヒドロキシ-3-カルボキシラト-1-プロパンアミニウム(+)-カルニチン(S)-3-カルボキシラト-2-ヒドロキシ-N,N,N-トリメチル-1-プロパンアミニウム(+)-ビタミンBT(3S)-3-ヒドロキシ-4-(トリメチルアザニウミル)ブタノアートD-Vitamin BTD-CARNITINEHCLCarnitine D-formD(+)-Carnitine,98%L-carnitine Impurity 1D(+)-Carnitine USP/EP/BPD-CARNITINE HYDROCHLORIDEDL-CARNITINE BENZYL ESTER CHLORIDE
CHEBI:11060S-(+)-3-hydroxy-4-trimethylaminobutyrate1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, hydroxide, inner salt, (S)-1-PROPANAMINIUM, 3-CARBOXY-2-HYDROXY-N,N,N-TRIMETHYL-, INNER SALT, (2S)-RefChem:130511L-I3-Trimethyl-I2-hydroxybutyrobetaine1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, hydroxide, inner salt, (S)-(9CI)625-884-0

データベース識別子

CAS
541-14-0
PubChem CID
2724480
ChEMBL
CHEMBL503189
ChEBI
CHEBI:11060
UNII
U9VY0ZOK7A
EC Number
625-884-0
Nikkaji
J94.155G

物性

構造計算による物性

XLogP
-0.2
極性表面積
60.4 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
3
重原子数
11

物理化学的性質

融点
197 °C · 197 °C
比旋光度
30.9 ° · D +30.9°
沸点
287.5 °C · 287.5°C (rough estimate)
比重(密度)
1.1587 · 1.1587 (rough estimate)
屈折率
1.45 · 1.4500 (estimate)
貯蔵温度
2 · Inert atmosphere,2-8°C

化学的性質

化学的特性white to light yellow crystal powde

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

毒性情報

Exposure RoutesIntravenous, Oral. Absolute bioavailability is 15% (tablets or solution). Time to maximum plasma concentration was found to be 3.3 hours.
Toxicity Summary · 1 件

Levocarnitine can be synthesised within the body from the amino acids lysine or methionine. Vitamin C (ascorbic acid) is essential to the synthesis of carnitine. Levocarnitine is a carrier molecule in the transport of long chain fatty acids across the inner mitochondrial membrane. It also exports acyl groups from subcellular organelles and from cells to urine before they accumulate to toxic concentrations. Only the L isomer of carnitine (sometimes called vitamin BT) affects lipid metabolism. Levocarnitine is handled by several proteins in different pathways including carnitine transporters, carnitine translocases, carnitine acetyltransferases and carnitine palmitoyltransferases.

Signs and SymptomsAdverse effects include hypertension, fever, tachycardia and seizures.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD<sub>50</sub> > 8g/kg (mouse, oral).

安全データ

wgk
3
rtecs
BP2979850
hs_code
29391900
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36-37/39

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

After oral administration L-carnitine which is unabsorbed is metabolized in the gastrointestinal tract by bacterial microflora. Major metabolites include trimethylamine N-oxide and [3H]-gamma-butyrobetaine. Route of Elimination: Following a single intravenous dose, 73.1 +/- 16% of the dose was excreted in the urine during the 0-24 hour interval. Post administration of oral carnitine supplements, in addition to a high carnitine diet, 58-65% of the administered radioactive dose was recovered from urine and feces in 5-11 days. Half Life: 17.4 hours (elimination) following a single intravenous dose.

用途と製造

Uses · 1 件

For treatment of primary systemic carnitine deficiency, a genetic impairment of normal biosynthesis or utilization of levocarnitine from dietary sources, or for the treatment of secondary carnitine deficiency resulting from an inborn error of metabolism such as glutaric aciduria II, methyl malonic aciduria, propionic acidemia, and medium chain fatty acylCoA dehydrogenase deficiency. Used therapeutically to stimulate gastric and pancreatic secretions and in the treatment of hyperlipoproteinemias. Parenteral levocarnitine is indicated for the prevention and treatment of carnitine deficiency in patients with end-stage renal disease.

応用分野 · 1 件

使用Essential cofactor of fatty acid metabolism; required for the transport of fatty acids through the inner mitochondrial membrane. Synthetized primarily in the liver and kidney; highest concentrations found in heart and skeletal muscle. Dietary sources include red meat, dairy products, beans, avocado.

調製方法 · 1 件

純化方法The S(L) isomer is levocarnitine, Vitamin B7. The R or S isomers crystallise from EtOH/Me2CO (hygroscopic). The R or S hydrochlorides crystallise from hot EtOH or EtOH/Et2O and have m 142o(dec). The RS-isomer crystallises from hot EtOH (hygroscopic). The RS hydrochloride crystallises in needles from hot EtOH and has m 196o(dec). [(±) Mazzetti & Lemmon J Org Chem 22 228 1957, Beilstein 4 H 513, 4 I 548, 4 II 937-8, 4 III 1632-5, 4 IV 3185.]

上流・下流製品情報

下流製品

サプライヤー101 社

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]

補足説明

定義ChEBI: The (S)-enantiomer of carnitine.

関連反応

5 件

化合物ノート

読み込み中…