基本情報
- CAS
17629-30-0- 標準SMILES
OC[C@H]1O[C@H](OC[C@H]2O[C@H](O[C@]3(CO)O[C@H](CO)[C@@H](O)[C@@H]3O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O- InChIKey
MUPFEKGTMRGPLJ-ZQSKZDJDSA-N- 分子式
- C18H32O16
- 平均分子量
- 504.4 g/mol
- 単同位体質量
- 504.16903494
概要
Raffinose is a trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 16 and 12 glycosidic linkages, respectively. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite and a plant metabolite. It is a trisaccharide and a raffinose family oligosaccharide.
名称と識別子
- 優先名称
- Raffinose
- IUPAC
- (2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
- 現地名
- D-(+)-ラフィノース五水和物
- 英語名
- D(+)-Raffinose pentahydrate
- 分子式
- C18H42O21
- 分子量
- 594.51
名称と別名
RAFFINOSEMelitose512-69-6D-RaffinoseGossyposeMelitriose6G-alpha-D-galactosylsucroseRaffinose, pureN5O3QU595MDTXSID8041111CHEBI:16634NSC-2025
名称をさらに表示
D-(+)-ラフィノース五水和物メリトース五水和物D(+)‐ラフィノース五水和物D(+)-ラフィノース(5水和物)D(+)-ラフィノース五水和物D-ラフィノース五水和物D-(+)-ラフィノースPENTAHYDRATERAFFINOSE RESEARCH GRADEラフィノース五水和物, D-(+)-D-(+)-ラフィノース 五水和物D-(+)-ラフィノース五水和物, 99%RAFFINOSE PENTAHYDRATED-(+)-RAFFINOSED-RAFFINOSE PENTAHYDRATEβ-D-fructofuranosideD-(+)-RAFFINOSE PENTAHYDRATERaffinose, 99%+Cottonseed sugarRAFFINOSE, 5-HYDRATED-(+)-Raffinose
alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1-6)-(2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triolNSC-170228(2S,3R,4S,5R,6R)-2-(((2R,3S,4S,5R,6R)-6-((2S,3S,4S,5R)-2,5-bis(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl)oxy-3,4,5-tris(oxidanyl)oxan-2-yl)methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol(2S,3R,4S,5R,6R)-2-(((2R,3S,4S,5R,6R)-6-((2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl)oxy-3,4,5-trihydroxyoxan-2-yl)methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol(2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-2,5-bis(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]oxy-3,4,5-tris(oxidanyl)oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triolRefChem:9106GlyTouCan:G40178VU
物性
構造計算による物性
- XLogP
- -5.8
- 極性表面積
- 269 Ų
- 水素結合供与体数
- 11
- 水素結合受容体数
- 16
- 回転可能結合数
- 8
- 重原子数
- 34
- 形式電荷
- 0
- 複雑度
- 655
実験および物理化学的性質
Chemical ClassesBiological Agents -> Oligosaccharides
SpringerMaterials PropertiesDensity
Solubility203 mg/mL
Melting Point80 °C
Physical Description
Pentahydrate: Solid; [Merck Index] Solid; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
208.9 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
209 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
208.72 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
210 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine]
197 Ų [M-H]-
210.51 Ų [M+HCOO]-
物理化学的性質
- 融点
- 78 · 78-80 °C
- 比旋光度
- 105 · 105 º (c=10,water,dry basis)
- 沸点
- 78 · 78-82℃
- 比重(密度)
- 1.465 · 1.465
- 貯蔵温度
- Inert atmosphere,Room Temperature
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
This chemical does not meet GHS hazard criteria for 100% (34 of 34) of all reports.
Not Classified
Aggregated GHS information provided per 34 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory InformationChemical: .alpha.-D-Glucopyranoside, .beta.-D-fructofuranosyl O-.alpha.-D-galactopyranosyl-(1.fwdarw.6)-
Other Safety InformationIMAP assessments - .alpha.-D-Glucopyranoside, .beta.-D-fructofuranosyl O-.alpha.-D-galactopyranosyl-(1.fwdarw.6)-: Human health tier I assessment
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified
安全データ
- F
- 3
- wgk
- 3
- tsca
- Yes
- rtecs
- LZ5851200
- hs_code
- 29400000
- risk_code
- 36/38
- hazard_code
- Xi
- safety_code
- 24/25-37/39-26
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Tissue LocationsPlatelet
Cellular LocationsCytoplasm
Metabolite PathwaysGalactose Metabolism
用途と製造
Uses
A trisaccharide composed of 1 mol each of D-galactose, D-glucose, and D-fructose; Found in Australian manna and cottonseed meal; [Merck Index]
Use (kg; approx.) in Germany (2009): >10
General Manufacturing Information.alpha.-D-Glucopyranoside, .beta.-D-fructofuranosyl O-.alpha.-D-galactopyranosyl-(1.fwdarw.6)-: ACTIVE
応用分野
用途糖研究用、ビフィズス菌増殖剤。
説明D-(+)-Raffinose is a trisaccharide composed of galactose, glucose, and fructose that occurs naturally in a variety of vegetables and grains. It is hydrolyzed to galactose and sucrose by α-galactosidase.
調製方法
Raffinose occurs naturally in Australian manna, cottonseed meal, and seeds of various food legumes. It can be isolated from beet sugar molasses through sucrose separation, seed-crystallization, and filtration.
純化方法fructo-furanose [17629-30-0 (5H2O), 512-69-6 (anhydrous)] M 594.5, m 8 0o, 80 -82o, +124o (c 10, H2O), [ ] D +105o (c 1 for pentahydrate, H2O), pK 1 12.40, pK 2 13.44, pK 3 13.52. D(+)-Raffinose crystallises from H2O, 90% aqueous EtOH or MeOH as the pentahydrate. The anhydrous sugar has m 132-135o. It has RF 0.8 on TLC (Silica Gel, and 1:3:3 CHCl3/butanone:/MeOH). The undecaacetate has been purified through an alumina column by elution with CHCl3, and recrystallised from EtOH/MeOH/H2O (3:2:5), with m 99-100o, [] D +92.8o (c 5.14, EtOH). [pK : Coccioli & Vicedomini Ann Chim (Rome) 66 269, 275 1976, 1H NMR: Suami et al. Carbohydr Research 26 234 1973, Beilstein 17 III/IV 3801, 17/8 V 403.]
関連反応
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化合物ノート
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