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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 134
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
- 溶解性
- メタノール(微量)、水(微量)
- 外見
- 個体
- 色
- ホワイトからオフホワイト
- Merck
- 13 · 13,1862
- 安定性
- Hygroscopic
- InChI
- InChI=1/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/s3
- InChIKey
- PHIQHXFUZVPYII-ISZMHOAENA-N
- SMILES
- C([C@@H](O)CC(=O)[O-])[N+](C)(C)C |&1:1,r|
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
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
毒性情報
Toxicity Summary
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.
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
- hazard_class
- IRRITANT
化学と産業
薬理情報
Metabolism/Metabolites
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
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
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
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
補足説明
定義ChEBI: The (S)-enantiomer of carnitine.
関連反応
化合物ノート
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