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β-アラニン

Beta-Alanine

HCID 239
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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
107-95-9
標準SMILES
NCCC(=O)O
InChIKey
UCMIRNVEIXFBKS-UHFFFAOYSA-N
分子式
C3H7NO2
平均分子量
89.09 g/mol
単同位体質量
89.04767847

概要

Beta-alanine is a naturally-occurring beta-amino acid comprising propionic acid with the amino group in the 3-position. It has a role as a neurotransmitter, an inhibitor, an agonist, a human metabolite and a fundamental metabolite. It is a conjugate acid of a beta-alaninate. It is a tautomer of a beta-alanine zwitterion.

名称と識別子

優先名称
Beta-Alanine
IUPAC
3-aminopropanoic acid
現地名
β-アラニン
英語名
β-Alanine
分子式
C3H7NO2
分子量
89.09

名称と別名

beta-alanine107-95-93-Aminopropanoic acid3-Aminopropionic acidAbufeneBeta Alaninebeta-Aminopropionic acid2-Carboxyethylamineomega-Aminopropionic acid3-AminopropanoateFEMA No. 325211P2JDE17B
名称をさらに表示
β-アラニンアブフェン3-アミノプロピオン酸β-アミノプロピオン酸3-アミノプロパン酸βアラニン3-アミノプロピオン酸(β-アラニン)Β‐アラニンベータアラニンβ-AlaB-ALANINEH-β-Ala-OHBETA-ALAAnalineBeta alanine powderFEMA 3252
I2-AlanineNSC-7603beta Alanine HydrochlorideDTXSID0030823CHEBI:169583 Aminopropionic AcidRefChem:567109Hydrochloride, beta-Alanine

データベース識別子

CAS
107-95-9、28854-76-4
PubChem CID
239
DTXSID
DTXSID0030823
ChEMBL
CHEMBL297569
ChEBI
CHEBI:16958
UNII
11P2JDE17B
EC Number
203-536-5
Nikkaji
J4.070C

物性

構造計算による物性

XLogP
-3
極性表面積
63.3 Ų
水素結合供与体数
2
水素結合受容体数
3
回転可能結合数
2
重原子数
6
形式電荷
0
複雑度
52.8

実験および物理化学的性質

Chemical ClassesOther Uses -> Biochemical Research
Drugs · 2 件

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

LogP-3.05
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 3 件

545.0 mg/mL

Soluble in water; Insoluble in ether and acetone

Slightly soluble (in ethanol)

Dietary IngredientsBeta-alanine
Melting Point200 °C
Vapor Pressure0.00000005 [mmHg]
Physical Description · 3 件

Solid; [Merck Index] White crystalline solid; [Alfa Aesar MSDS]

Solid

Colourless needles;

Ionization Efficiency · 6 件

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 · 3 件

This chemical does not meet GHS hazard criteria for 98.5% (322 of 327) of all reports.

Not Classified

Aggregated GHS information provided per 327 reports by companies from 5 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 4 件

Chemical: .beta.-Alanine

Regulation (EC) No 1831/2003 (amended)

REACH registered substance: β-alanine (EC: 203-536-5)

.beta.-Alanine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] May cause eye irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesNot Classified

毒性情報

Health EffectsChronically high levels of beta-alanine are associated with at least 2 inborn errors of metabolism including: GABA-Transaminase Deficiency and Methylmalonate Semialdehyde Dehydrogenase Deficiency.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

wgk
3
tsca
TSCA listed

化学と産業

薬理情報

Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysAspartate Metabolism

用途と製造

Uses · 4 件

Used to make pantothenic acid and derivatives and as a buffer in electroplating; [Merck Index] Used as flavoring agent or adjuvant and nutritional supplement; [FDA] An amino acid not found in protein; Used in organic synthesis and biochemical research; [Alfa Aesar MSDS]

Electroplating [Category: Plate]

Use (kg; approx.) in Germany (2009): >1000

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Use Classification · 3 件

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information.beta.-Alanine: ACTIVE
応用分野 · 5 件

用途β-アラニン(3-aminopropionic acid):略号β-Ala.タンパク質構成成分としてではなく遊離の形で,またはパントテン酸,コエンザイムA,カルノシン,アンセリンなどのなかに含まれる.アクリル酸やアクリロニトリルとアンモニアから合成される.淡い甘味のある斜方晶系(水).分解点197~198 ℃.水に易溶,有機溶媒に不溶.パントテン酸製造原料.

説明β-Alanine (or beta-alanine) is a naturally occurring beta amino acid, which is an amino acid in which the amino group is at the β- position from the carboxylate group (i.e., two atoms away. The IUPAC name for β-alanine is 3-amino propanoic acid. Unlike its counterpart α-alanine, β-alanine has no stereocenter. β-Alanine is not used in the biosynthesis of any major proteins or enzymes. It is formed in vivo by the degradation of dihydrouracil and carnosine. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (vitamin B5), which itself is a component of coenzyme A. Under normal conditions, β-alanine is metabolized into acetic acid. β-Alanine is the rate-limiting precursor of carnosine, which is to say carnosine levels are limited by the amount of available β-alanine. Supplementation with β-alanine has been shown to increase the concentration of carnosine in muscles, decrease fatigue in athletes and increase total muscular work done.Typically, studies have used supplementing strategies of multiple doses of 400 mg or 800 mg, administered at regular intervals for up to eight hours, over periods ranging from 4 to 10 weeks . After a 10 - week supplementing strategy, the reported increase in intramuscular carnosine content was an average of 80.1% (range 18 to 205%).

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1 / 70 ページ

化合物ノート

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Positive

2.15

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Dissociation Constants · 2 件

10.2

3.63 (at 5 °C)

物理化学的性質

融点
202 °C · 202 °C (dec.)(lit.)
沸点
237.1 · 237.1±23.0 °C(Predicted)
比重(密度)
1 · 1,437 g/cm3
屈折率
1.465 · 1.4650 (estimate)
FEMA
3252 · 3252 | BETA-ALANINE
闪点
204 · 204-206°C
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature
溶解性
2 O: · H2O: 1M at20℃、透明、無色
酸解離定数(Pka)
3.55 · 3.55(at 25℃)
外見
結晶性粉末
色
白い
PH
6 · 6.0-7.5
臭い (Odor)
100 %で。無臭 · 100.00%で。無臭
においのタイプ
無臭
由来生物
synthetic
水溶解度
水に溶けます (550g/L)。アルコールにわずかに溶ける。エーテル、アセトンに不溶。
Decomposition
204 · 204-206 ºC
Merck
14 · 14,205
JECFA Number
1418 · 1418
BRN
906793 · 906793
安定性
安定。乾いた状態に保ちます。
化粧品成分の機能
保湿剤
InChI
1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
InChIKey
UCMIRNVEIXFBKS-UHFFFAOYSA-N
SMILES
NCCC(O)=O || NCCC(O)=O
LogP
-0.882 · -0.882 (est)
CAS データベース
107 · 107-95-9(CAS DataBase Reference)
NISTの化学物質情報
Beta-alanine(107-95-9)
EPAの化学物質情報
.beta.-Alanine (107-95-9)
化学的性質 · 1 件

化学的特性This is a secondary amino acid, which is formed in vivo by the degradation of dihydrouracil and carnosine. Because neuronal uptake and neuronal receptor sensitivity to β-alanine have been demonstrated, the compound may be a false transmitter replacing GABA. A rare genetic disorder, hyper-β-alaninemia, has been reported. It is used as a flavor enhancer, flavoring agent, nutrient supplement or adjuvant. β-Alanine has a slightly sweet taste.

rtecs
UA2369200
hs_code
2922499990
risk_code
36/37/38
化審法
(9)-1554
hazard_code
Xi
safety_code
24/25-36-26
ストレージクラス
11 - Combustible Solids

天然物の起源Reported to occur as a component in amino acids; carnosine, anserine, pantothenic acid

使用β-Alanine is a naturally occurring beta amino acid. β-Alanine is formed in vivo by the degradation of dihydrouracil (D449990) and carnosine. β-Alanine is also the rate-limiting precursor of carnosine, as a result supplementation with β-alanine increases the concentration of carnosine in muscles.

一般的な説明An N-blocked form of alanine.

調製方法 · 2 件

製造方法By heating acrylic acid with concentrated aqueous ammonia under pressure, by addition of acrylonitrile to phthalimide or to ammonia; from β-aminopropionitrile, from succinimide by the Hofmann degradation.

純化方法Crystallise β-alanine by dissolving it in a hot saturated aqueous solution, filtering, adding four volumes of absolute EtOH and cooling in an ice-bath. Recrystallise it in the same way and then finally, crystallise it from a warm saturated solution in 50% EtOH and adding four volumes of absolute EtOH with cooling in an ice-bath. The crystals are dried in a vacuum desiccator over P2O5. [Donovan & Kegeles J Am Chem Soc 83 255 1961, Beilstein 4 IV 2526.]

上流・下流製品情報

上流原料

次亜塩素酸ナトリウム3-アミノプロピオニトリルこはく酸イミドアンバージェットR4200-CLジフェニルアミンActivated carbon,decolor

下流製品

N-t-Boc-β-alanineジ(β-アラニン)カルシウム3-マレイミドプロピオン酸DL-パントテン酸 カルシウムβ-アラニンTERT-ブチルエステル塩酸塩Ethyl 3-(isopropylamino)propanoate3-[N-[N-[(2,2-ジメチル-2,3-ジヒドロベンゾフラン-7-イル)オキシカルボニル]-N-メチルアミノチオ]-N-イソプロピルアミノ]プロピオン酸エチルD-パントテン酸カルシウム4-フルオロ-α-(2-メチル-1-オキソ-プロピル)-γ-オキソ-N-β-ジフェニルベンゼン ブタンアミドL-アラニンペンタガスリン5-クロロ-1H-インダゾール-3-酢酸セリトンブルーGF-3Rパミドロン酸N-hydroxyethyl-N-hydroxyalkyl-β-alanine1-(tert-ブトキシカルボニル)-4-ピペリドンethyl 3-(chlorosulfanyl-propan-2-yl-amino)propanoateD-パントテン酸3-アミノプロピオンアルデヒド

補足説明

定義ChEBI: A naturally-occurring beta-amino acid comprising propionic acid with the amino group in the 3-position.