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L-(+)-アラビノース

L-Arabinose

HCID 439195
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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
5328-37-0
標準SMILES
OC1OC[C@H](O)[C@H](O)[C@H]1O
InChIKey
SRBFZHDQGSBBOR-HWQSCIPKSA-N
分子式
C5H10O5
平均分子量
150.13 g/mol

概要

L-arabinopyranose is the six-membered ring form of L-arabinose. It has a role as a mouse metabolite and an Escherichia coli metabolite.

名称と識別子

優先名称
L-Arabinose
IUPAC
(3R,4S,5S)-oxane-2,3,4,5-tetrol
現地名
L-(+)-アラビノース
英語名
L-Arabinose
分子式
C5H10O5
分子量
150.13

名称と別名

L-ARABINOPYRANOSEarabinopyranosideL-ArabinopyranosideL-AraArabinopyranoseArabinose l-SNFG:AraAra (SNFG)RefChem:53263GlyTouCan:G88980IRDTXCID7019733CHEBI:30849
名称をさらに表示
L-(+)-アラビノースL-アラビノース(+)-L-アラビノース(2R,3S,4S)-2,3,4,5-テトラヒドロキシペンタナールL-アラビノスアラビノース, L-(+)-β-L-アラビノースAmidosulfonic acidX-GAL (SOLID POWDERFEMA 3255pectinoseL- pentosePECTIN SUGARL(+)ArabinoseL(+)-ArbinoseL(+)-Gum sugar
ARAG88980IR226-214-65328-37-0ArabinoseArabinose, L-B40ROO395ZDTXSID9039733

データベース識別子

CAS
5328-37-0、87-72-9
PubChem CID
439195
ChEMBL
CHEMBL1357418、CHEMBL505348
ChEBI
CHEBI:17535
EC Number
201-767-6、226-214-6
Nikkaji
J192.647K

物性

構造計算による物性

XLogP
-2.5
極性表面積
90.2 Ų
水素結合供与体数
4
水素結合受容体数
5
回転可能結合数
0
重原子数
10
形式電荷
0
複雑度
117

実験および物理化学的性質

Chemical Classes · 2 件

Biological Agents -> Monosaccharides and Derivatives

Biological Agents -> Monosaccharides and Derivatives

CosmeticsCosmetic ingredients (Arabinose) -> CIR (Cosmetic Ingredient Review)
LogP-3.02
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Physical Description · 2 件

Colorless solid; [Merck Index]

White odorless powder; [Alfa Aesar MSDS]

Collision Cross Section · 2 件

141.86 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

134.6 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

物理化学的性質

融点
160 · 160-163 °C(lit.)
比旋光度
104 · 104 º (C=6, IN WATER 23 ºC)
沸点
415.5 · 415.5±38.0 °C(Predicted)
比重(密度)
1.508 · 1.508±0.06 g/cm3(Predicted)
蒸気圧
0 Pa · 0Pa at 20℃

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 · 6 件

This chemical does not meet GHS hazard criteria for 99.6% (227 of 228) of all reports.

Not Classified

Aggregated GHS information provided per 228 reports by companies from 2 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 100% (6 of 6) of all reports.

Not Classified

Aggregated GHS information provided per 6 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 5 件

Chemical: L-Arabinopyranose

Chemical: L-Arabinose

Status: Active Update: 13-11-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25105

L-Arabinose: Does not have an individual approval but may be used under an appropriate group standard

L-Arabinopyranose: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety Information · 2 件

IMAP assessments - L-Arabinose: Environment tier I assessment

IMAP assessments - L-Arabinopyranose: Environment tier I assessment

Hazards Summary · 2 件

May cause irritation; [Sigma-Aldrich MSDS]

May cause eye irritation; [Alfa Aesar MSDS]

Hazard Classes and Categories · 2 件

Not Classified

Not Classified

毒性情報

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

化学と産業

用途と製造

Uses · 2 件

CIR ingredient: Arabinose

Monosaccharide; The L-form is found in plants and mycobacteria; Used as a nutrient in bacterial culture media; [Merck Index] Used as a flavoring agent; [FDA]

General Manufacturing Information · 2 件

L-Arabinopyranose: ACTIVE

L-Arabinose: ACTIVE

応用分野 · 4 件

解説L-アラビノースは,多くの針葉樹の心材中に遊離状態で存在するほか,アラビアゴム,サクラゴム,ペクチン質などの多糖類構成成分として多量に存在する.これらの加水分解で得られる.β-ピラノース型は融点160 ℃[α]D+191→+104.5°(水).水に易溶,アルコール類に難溶.還元糖としての一般的性質を示す.ある種の酵母により発酵される.

説明L-Arabinose is considered a rare sugar that can be found naturally within the structures of most fruits and vegetables. Due to its low caloric sweetening effects, arabinose is commonly used in nutritional supplements and prescription drugs. In addition to its sweetening effects, when reacted with amino acid blends, using the Maillard Reaction, arabinose is able to contribute to the production of savory and meaty flavors used within the food and flavor industry.L-Arabinose is commonly used in the Flavor Industry to produce meaty or cooked/roasted flavors.

天然物の起源For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous to D-glyceraldehyde. However, L-arabinose is in fact more common than D-arabinose in nature and is found in nature as a component of biopolymers such as hemicellulose and pectin. L-Arabinose is widely distributed in nature including Acacia and Larix species as a complex polysaccharide.

使用The L-arabinose operon, also known as the araBAD operon, has been the subject of much biomolecular research. The operon directs the catabolism of arabinose in E. coli, and it is dynamically activated in the presence of arabinose and the absence of glucose. In synthetic biology, arabinose is often used as a one-way or reversible switch for protein expression under the Pbad promoter in E. coli. This on-switch can be negated by the presence of glucose or reversed off by the addition of glucose in the culture medium which is a form of catabolite repression. L-Arabinose is an arabinose isomer widely found in nature, while D-arabinose is less common. L-Arabinose is a constituent of many biopolymers that make up plant cell walls. This monosaccharide is often used in cell culture media, serving as a bacterial carbon source, and can be used to distinguish between bacteria based on their fermentation abilities. L-Arabinose, in the absence of glucose, induces transcription of the ara operon in E. coli that encodes L-arabinose catabolizing enzymes. It does this by binding to the AraC protein and activating the PBAD promoter. The PBAD promoter is used in plasmid vectors as a switch for protein expression that can be turned on by L-arabinose or turned off by addition of glucose.

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化合物ノート

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このページの内容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
屈折率
104 ° · 104 ° (C=10, H2O)
FEMA
3255 · 3255 | L-ARABINOSE
貯蔵温度
room temp
溶解性
2 O: · H2O: 1M at20℃、透明、無色
酸解離定数(Pka)
12.46 · 12.46±0.20(Predicted)
外見
個体
色
白色結晶
PH
6.5 · 6.5-7.0 (100g/l, H2O, 20℃)
臭い (Odor)
無臭
水溶解度
ほとんど透明
Merck
14 · 14,761
BRN
1723085 · 1723085
安定性
安定。強力な酸化剤とは相容れない。
InChI
1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m0/s1
InChIKey
PYMYPHUHKUWMLA-VAYJURFESA-N
SMILES
OC[C@H](O)[C@H](O)[C@@H](O)C=O
LogP
-2.8 at · -2.8 at 20℃
CAS データベース
5328 · 5328-37-0(CAS DataBase Reference)
EPAの化学物質情報
L-Arabinose (5328-37-0)
化学的性質 · 1 件

化学的特性L-Arabinose is a white crystalline powder, It is a rare type of C5-sugar that naturally occurs in the hemicelluloses structure of most fruits and vegetables. Its name is derived from gum Arabic, another well-known food ingredient. Humans have always consumed L-Arabinose both pure as well as part of the hemicelluloses structure. The highest concentrations of L-Arabinose in food as monosaccharide can be found in instant coffee, wine and sake.

安全データ

F
3-10
wgk
3
tsca
TSCA listed
hs_code
2940 00 00
ストレージクラス
11 - Combustible Solids

調製方法

製造方法By partial hydrolysis of mesquite gum.

上流・下流製品情報

上流原料

エラグ酸二水和物3,7,8-tri-O-methylellagic acidL-(+)-ラムノース一水和物D-(+)-グルコースD-(+)-ガラクトース (無水)

下流製品

3‐メチルエラグ酸D-(+)-キシロースL-erythro-2-ペンツロースL-Arabinose hydrazone

補足説明

定義l-enantiomers occur naturally. lArabinose is common in vegetable gums, especially arabic.