DL-Carnitine (HCID 288)

概要

Carnitine is an amino-acid betaine that is butanoate substituted with a hydroxy group at position C-3 and a trimethylammonium group at C-4. It has a role as a mouse metabolite and a human metabolite. It is functionally related to a butyrate. It is a conjugate base of a carnitinium.

名称と識別子

優先名称: DL-Carnitine
IUPAC: 3-hydroxy-4-(trimethylazaniumyl)butanoate
現地名: rac-(R*)-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
英語名: DL-Carnitine
分子式: C7H15NO3
分子量: 161.2

名称と別名

DL-CarnitineCarnitineCarnitina3-hydroxy-4-(trimethylazaniumyl)butanoateD,L-carnitineS7UI8SM58ANSC-757390CHEBI:17126(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner saltCarnitinumCHEBI:3424(3-carboxy-2-hydroxypropyl)-trimethylazanium

名称をさらに表示

rac-(R*)-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rac-(R*)-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(±)-カルニチン3-カルボキシ-2-ヒドロキシ-N,N,N-トリメチル-1-プロパンアミニウムDL-カルニチンN,N,N-トリメチル-3-カルボキシ-2-ヒドロキシ-1-プロパンアミニウムキャリヤーCardiogenCarrierCardiogen peptideCarnumMiocorC00487NovaineExcitineCARNITINCarnicor

Carnitine dl-RefChem:574690(3-carboxy-2-hydroxypropyl)trimethylazanium206-976-6406-76-8461-06-33-hydroxy-4-(trimethylammonio)butanoateCarnitine DL-form

データベース識別子

CAS: 406-76-8、541-15-1
PubChem CID: 288
DTXSID: DTXSID3022744
ChEMBL: CHEMBL172513
ChEBI: CHEBI:17126
UNII: S7UI8SM58A
EC Number: 206-976-6
Nikkaji: J1.347.334J

物性

構造計算による物性

XLogP: -0.2
極性表面積: 60.4 Å²
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

実験および物理化学的性質

Cosmetics · 2 件

Cosmetic ingredients (Carnitine) -> CIR (Cosmetic Ingredient Review)

Cleansing; Foam boosting

Dietary IngredientsCarnitine

Collision Cross Section131.39 Å² [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 197 · 197-198 °C (decomp)
貯蔵温度: -20 °C · Store at -20°C
溶解性: Soluble in DMSO
InChI: InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3
InChIKey: PHIQHXFUZVPYII-UHFFFAOYSA-N
SMILES: C(C(O)CC([O-])=O)[N+](C)(C)C

安全と法規制

危険有害性情報

Regulatory InformationCarnitine: Does not have an individual approval but may be used under an appropriate group standard

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 · 3 件

The CIR Expert Panel concluded the following ingredients are safe in the present practices of use and concentration described in the safety assessment when formulated to be non-irritating...Carnitine...

Safe for use in cosmetics, with qualifications

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

注意喚起語: 警告
危険有害性情報: コード危険有害性情報危険有害性クラス区分注意喚起語シンボル P コード H302

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 · 2 件

CIR ingredient: Carnitine

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.

Use ClassificationCosmetics -> Cleansing; Foam boosting

応用分野 · 2 件

解説① ⇒担体② 半導体中の伝導電子および価電子帯中の正孔のこと．電荷担体(charge carrier)というべきであるが，半導体の分野では単にキャリヤーとよばれる．③ 電子写真の現像剤に用いられ，トナーの運搬と摩擦帯電の役割を担う．粉体現像ではガラス球や鉄粉が用いられ，トナーと摩擦帯電すると同時にトナーを付着させ，静電潜像へ均一に供給する．液体現像では絶縁性の有機溶媒が用いられ，帯電したトナーを均一に分散させる役目をする．④ 疎水性繊維に吸着，拡散して繊維を可塑化し，染料が繊維内部に容易に拡散しうるようにする助剤(染色速度促進剤)．

使用DL-Carnitine is a Chloride salt free form of D,L-Carnitine Chloride (C184100). Carnitine is a vitamin, essential cofactor of fatty acid metabolism. It is required for the transport of fatty acids through the inner mitochondrial membrane. Synthesized primarily in the liver and kidney; highest concentrations found in heart and skeletal muscle. Dietary sources include red meat, dairy products, beans, avocado.