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[ソラニダ-5-エン-3β-イル]2-O-(6-デオキシ-α-L-マンノピラノシル)-3-O-(β-D-グルコピラノシル)-β-D-ガラクトピラノシド

alpha-Solanine

HCID 9549171
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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
20562-02-1
標準SMILES
C[C@H]1CC[C@@H]2[C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)CC[C@]6(C)[C@H]5CC[C@]34C)N2C1
InChIKey
ZGVSETXHNHBTRK-UDJLNJFBSA-N
分子式
C45H73NO15
平均分子量
868.1 g/mol
単同位体質量
867.49802062

概要

Solanine is a glycoalkaloid poison found in species of the nightshade family (Solanaceae), such as the potato (Solanum tuberosum). It is a trisccharide derivative of solanidine [(22beta)-solanid-5-en-3beta-ol]. It has a role as an antineoplastic agent, a phytotoxin, an apoptosis inducer and a plant metabolite. It is a glycoalkaloid, an organic heterohexacyclic compound, a steroid saponin and a trisaccharide derivative. It is functionally related to a solanidine.

名称と識別子

優先名称
alpha-Solanine
IUPAC
(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
現地名
[ソラニダ-5-エン-3β-イル]2-O-(6-デオキシ-α-L-マンノピラノシル)-3-O-(β-D-グルコピラノシル)-β-D-ガラクトピラノシド
英語名
alpha-Solanine
分子式
C45H73NO15
分子量
868.06

名称と別名

alpha-Solanine20562-02-1DTXSID9030707RefChem:111392DTXCID601527922(2R,3R,4R,5R,6S)-2-((2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-(((1S,2S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol2-((3-hydroxy-2-(hydroxymethyl)-6-((10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)oxan-4-yl)oxy)-6-(hydroxymethyl)oxane-3,4,5-triolSolanina-solanine51938-42-2UNII-3FYV8328OKMLS000517299
名称をさらに表示
ソラニダ-5-エン-3β-イル2-O-(6-デオキシ-α-L-マンノピラノシル)3-O-(β-D-グルコピラノシル)-β-D-ガラクトピラノシドソラニダ-5-エン-3β-イル2-O-(6-デオキシ-α-L-マンノピラノシル)-3-O-(β-D-グルコピラノシル)-β-D-ガラクトピラノシドソラニンα-ソラニン

物性

構造計算による物性

XLogP
1.8
極性表面積
241 Ų
水素結合供与体数
9
水素結合受容体数
16
回転可能結合数
8
重原子数
61
形式電荷
0
複雑度
1,590

実験および物理化学的性質

Chemical ClassesBiological Agents -> Plant Toxins
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Solanidines and alkaloid derivatives [ST0115]
Color/FormSLENDER NEEDLES FROM 85% ALC
Solubility · 2 件

DECOMP ABOUT 212 °C; USUALLY AMORPHOUS & GUMMY BUT HAS BEEN CRYSTALLIZED; SOL IN WATER /SOLANINE HYDROCHLORIDE/

READILY SOL IN HOT ALC, PRACTICALLY INSOL IN WATER (25 MG/L @ PH 6.0), ETHER, CHLOROFORM

Optical RotationSPECIFIC OPTICAL ROTATION: -60 DEG @ 20 °C/D (PYRIDINE)
Physical DescriptionSolid; [Merck Index] White odorless solid; [MSDSonline]
Dissociation ConstantsPK @ 15 °C= 6.66; K= 2.2X10-7
Other Experimental PropertiesBROWNS AND SINTERS ABOUT 190 °C; DECOMP ABOUT 285 °C

物理化学的性質

融点
285 ℃ · 285℃ (dec.)

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 · 4 件

Warning

H302 (97.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazards Summary · 1 件

In Britain, potatoes are the most common cause of solanine poisoning of farm animals, usually pigs; Large amounts of this alkaloid are produced as potatoes turn green on exposure to light; Old and unripe or sprouted and rotten tubers also pose a threat; Emergency treatment: Plants- solanine; Solanine causes nausea, vomiting, headache, diarrhea, and possibly drowsiness and coma. [HSDB] Solanine poisoning is uncommon in humans. Ingestion of 2-5 grams of green parts of potatoes/kg body weight is not likely to cause acute toxicity. [Goldfrank, p. 1545]

Special ReportsA REVIEW WITH 23 REFERENCES ON THE CHEM, PHARMACOLOGY, AND TOXICITY OF SOLANINE.[DALVI RR, BOWIE WC; TOXICOLOGY OF SOLANINE: AN OVERVIEW; VET HUM TOXICOL 25(1) 13 (1983)]
Hazard Classes and CategoriesAcute Tox. 4 (97.7%)

毒性情報

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity Summary · 1 件

Solanum glycoalkaloids can inhibit cholinesterase, disrupt cell membranes, and be teratogenic (cause birth defects). One study suggests that the toxic mechanism of solanine is caused by the chemical's interaction with mitochondrial membranes. Experiments show that solanine exposure opens the potassium channels of mitochondria, decreasing their membrane potential. This in turn leads to Ca2+ being transported from the mitochondria into the cytoplasm, and it is this increased concentration of Ca2+ in the cytoplasm that triggers cell damage and apoptosis. (Wikipedia)

化学と産業

用途と製造

Uses · 4 件

Found in the Solanum species (especially potatoes); Has been used as an agricultural insecticide; [Merck Index]

Farming (Pesticides) [Category: Industry]

HAS BEEN USED AS AN AGRICULTURAL INSECTICIDE /SOLANINE HYDROCHLORIDE/

alpha-Solanine is found in alcoholic beverages.

Use ClassificationFood Contaminant -> NATURALLY_OCCURRING_TOXICANT -> JECFA Functional Classes
General Manufacturing Information · 2 件

EXTRACTION PROCEDURE: SOLTYS, WALLENFELS, BER 69, 811 (1936). SEPARATED BY CHROMATOGRAPHY INTO SIX COMPONENTS: ALPHA-, BETA-, GAMMA-SOLANINE AND ALPHA-, BETA-, AND GAMMA-CHACONINE. MAIN CONSTITUENT ALPHA-SOLANINE...

TREATMENT OF POTATO TUBERS @ 22 DEG WITH CORN OIL, PEANUT OIL, OLIVE OIL, VEGETABLE OIL, OR MINERAL OIL INHIBITED SOLANINE FORMATION. THE MINIMUM EFFECTIVE CONCN FOR THE INHIBITION OF SOLANINE FORMATION CONSISTED OF 1/8 CORN OIL PLUS 7/8 ACETONE SOLN.

応用分野 · 4 件

解説ソラニン．ソラツニンともいう．ジャガイモの新芽およびトマトに含まれるステロイドアルカロイドの配糖体．エタノールから針状晶として得られる．分解点285 ℃．[α]20D－59°(ピリジン)．アグリコンはソラニジン，糖はD-ガラクトース，D-グルコース，L-ラムノースよりなる(図)．原形質毒で，強力な溶血作用があり，頭痛，吐き気，胃炎などの中毒症状を起こすが，致命傷になることはまれである．農業用殺虫剤に用いられる．LD50 42 mg/kg(マウス，腹腔内)．

説明This steroidal alkaloid is present in several Solanum species including S. nigrum, S. Iycopersicum (tomato) and S. tuberosum (potato). The base crystallizes in slender needles and shrinks markedly at 235°C. It has [α]20D - 59.45° (pyridine) or - 42.16° (dilute HCl) and is readily soluble in hot EtOH, sparingly so in H20 and virtually insoluble in CHCl 3 or Et2 0. The salts are mostly amorphous although a crystalline hydrochloride has been prepared with m.p. 212°C (dec.). It is not affected by alkalies but mineral acids hydrolyze it to solanidine (q.v.) and one mole each of dextrose, galactose and rhamnose.Pharmacologically, the alkaloid is a protoplasmic poison and a powerful haemolytic. Poisoning by potatoes sometimes occurs although the results are not usually fatal. The symptoms are nausea, headache, emesis and gastritis. With large doses parenchymatous nephritis and haemoglobinuria occurs with, at times, paralysis of the central nervous system and cardiac arrest. The alkaloid also possesses local irritant properties.

関連反応

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化合物ノート

読み込み中…

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
その他の操作
ノートを作成反応を作成見積依頼を出す
[ソラニダ-5-エン-3β-イル]2-O-(6-デオキシ-α-L-マンノピラノシル)-3-O-(β-D-グルコピラノシル)-β-D-ガラクトピラノシド
3β-[2-O-(6-デオキシ-α-L-マンノピラノシル)-3-O-(β-D-グルコピラノシル)-β-D-ガラクトピラノシルオキシ]ソラニダ-5-エン
Α‐ソラニン
ソラニン, Α-(SOLATUNIソラツニン
solanine
α-Solanine
SOLATUNIN
α-Solanin
SOLATUNINE
ALPHA-SOLANIN
α-Solanine-RM
α-Solanine ,99%
MLS001074921MFCD00077873(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triolSMR000127418beta-D-Galactopyranoside, (3beta)-solanid-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-solanid-5-en-3beta-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)]-beta-D-galactopyranoside-Solanine|_-Solanine

データベース識別子

CAS
20562-02-1、51938-42-2
PubChem CID
9549171
DTXSID
DTXSID9030707
ChEMBL
CHEMBL1392894
ChEBI
CHEBI:9188
EC Number
243-879-8
Nikkaji
J16.241H
沸点
780.78 °C · 780.78°C (rough estimate)
比重(密度)
1.4 · 1.40±0.1 g/cm3 (20 ºC 760 Torr)
屈折率
1.528 · 1.5280 (estimate)
貯蔵温度
20 °C · −20°C
溶解性
メタノール（マイルド、加熱）、ピリジン（マイルド、超音波処理）、
外見
個体
酸解離定数(Pka)
6.66 · 6.66(at 15℃)
色
ホワイトからオフホワイト
水溶解度
26.04 mg/L · 26.04mg/L(15℃)
Merck
13 · 13,8779
BRN
77607 · 77607
InChIKey
ZGVSETXHNHBTRK-MUEWWJAYNA-N
LogP
5.67 · 5.670 (est)

化学的性質

化学的特性White solid

Plant Concentrations · 1 件

SAMPLES OF RAW AND COOKED POTATO PEELS FROM COMMERCIAL POTATO VARIETIES WERE ANALYZED FOR THEIR ALPHA-SOLANINE CONTENT BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY (HPLC). RAW PEELS CONTAINED 0.5-50.16 MG/100 G PEEL (WET WT) OF ALPHA-SOLANINE. RAW FLESH FROM THE SAME POTATOES CONTAINED 0.01-2.18 MG/100 G FLESH (WET WT) OF ALPHA-SOLANINE. FRIED PEELS CONTAINED MORE ALPHA-SOLANINE (1.09-72.09 MG/100 G).

Natural Pollution Sources · 2 件

FROM SOLANUM SPECIES, ESP FROM S TUBEROSUM L (POTATO), S NIGRUM L (WOODY NIGHTSHADE), AND LYCOPERSICON ESCULENTUM MILL, SOLANACEAE (TOMATO). FRESH POTATO SPROUTS CONTAIN ABOUT 0.04%.

THE TUBER OF THE POTATO IS THE COMMONEST SOURCE OF POISONING FROM SOLANINE IN FARM ANIMALS IN BRITAIN, AND PIGS ARE THE ANIMALS USUALLY AFFECTED, BUT THE FEEDING OF GREEN POTATO HAULMS HAS CAUSED GREAT LOSSES IN EUROPE. POTATOES WHEN EXPOSED TO LIGHT BECOME GREEN: DURING THE PROCESS LARGE QUANTITIES OF SOLANINE ARE FORMED AND RENDER THE GREEN PARTS EXTREMELY POISONOUS. UNRIPE AND OLD, ROTTEN OR SPROUTING TUBERS WHICH HAVE BEEN KEPT FOR A LONG TIME ARE ALSO DANGEROUS. THE ALKALOID IS PRESENT IN THE GREATEST CONCN IN THE "EYES", SKIN AND THE YOUNG GREEN SPROUTS.

Human Toxicity Excerpts · 2 件

LOW CONCN OF ALPHA-SOLANINE STIMULATED THE GROWTH OF CULTURED HUMAN FIBROBLASTS, WHILE HIGHER CONCN (GREATER THAN 30 MUG/ML) HAD A MARKEDLY INHIBITORY EFFECT. AUTORADIOGRAPHIC STUDIES INDICATED THAT THE STIMULATION OF CELL GROWTH WAS DUE TO A SHORTENING OF THE G1 PHASE. FEULGEN MICRODENSITOMETRY OF CELLS TREATED WITH HIGH DOSES OF ALPHA-SOLANINE REVEALED AN ABNORMAL ACCUM OF CELLS IN G2. BY VIRTUE OF EITHER ITS STIMULATORY OR ITS INHIBITORY EFFECT ON CELL GROWTH, ALPHA-SOLANINE COULD ACT AS A HUMAN TERATOGEN.

FATAL POISONING HAS BEEN DESCRIBED FROM THE INGESTION OF SPROUTING POTATOES, BUT THE USUAL CONCN IN POTATOES (LESS THAN 0.01%) HAS NO TOXIC SIGNIFICANCE.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 5 件

/SOLANINE/...EXERTS A DIRECT IRRITANT EFFECT ON THE MUCOUS MEMBRANES OF THE ALIMENTARY TRACT AND, ON ABSORPTION INTO THE BLOOD STREAM, BRINGS ABOUT HEMOLYSIS OF THE RED CELLS. IT ALSO PRODUCES CENTRAL NERVOUS SYSTEM STIMULATION FOLLOWED BY DEPRESSION, DEPRESSION OF THE RESP AND MOTOR CENTERS AND, IN LARGE DOSES, CARDIAC ARREST.

...TYPES OF POISONING FROM INGESTION OF POTATOES: 1) A NERVOUS FORM IN WHICH SIGNS OF STUPOR AND DEPRESSION PREDOMINATE; THIS IS USUALLY SEEN TOGETHER WITH 2) THE GASTRIC TYPE, CHARACTERIZED BY SALIVATION, VOMITING, DIARRHEA AND OTHER SIGNS OF GI IRRITATION; AND 3) AN EXANTHEMATOUS FORM, ASSOC WITH ULCERATIVE STOMATITIS, CONJUNCTIVITIS, DIARRHEA AND A VESICULAR AND SCURFY ECZEMA OF THE LEGS.

IN HORSES, CATTLE, PIGS AND POULTRY, THE NERVOUS TYPE /OF POISONING FROM INGESTION OF POTATOES/ APPEARS TO PREDOMINATE; DULLNESS, PROSTRATION AND TOTAL INDIFFERENCE TO THE ENVIRONMENT BEING THE MOST COMMON SIGNS.

SOLANINE...HAS BEEN TESTED FOR TERATOGENICITY IN CHICK EMBRYOS... TEN TO 25 MG WAS ADMIN ON THE 4TH DAY OF INCUBATION TO THE CHICK AND NO INCR IN CONGENITAL MALFORMATIONS WAS FOUND. ...RATS /WERE FED/ A DIET CONTAINING 10 PERCENT POTATO SPROUTS FROM THE TIME PREGNANCY WAS INDICATED BY INCR WT GAIN. NO DEFECTS WERE DETECTED BUT THE PUPS DIED BEFORE WEANING. ...FOUND NO CONGENITAL DEFECTS IN RATS AFTER THEY ADMIN UP TO 25 MG PER KG ON DAYS 8 THROUGH 11 /OF PREGNANCY/.

For more Non-Human Toxicity Excerpts (Complete) data for SOLANINE (6 total), please visit the HSDB record page.

安全データ

F
10
wgk
3
rtecs
WF0250000
ridadr
1544
hs_code
29399990
risk_code
22
hazard_code
Xn
safety_code
1-25-45-24/25
hazard_class
6.1(b)
packing_group
III
Hazard Classifications
Acute Tox. 4 Oral
ストレージクラス
11 - Combustible Solids
有毒物質データの
20562-02-1(Hazardous Substances Data)

使用α-Solanine is produced as a by product in the synthesis of α-Chaconine. α-Chaconine is a glycoalkaloid displaying nerve toxin activity. Potential antifungal activity.

一般的な説明This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

調製方法 · 1 件

純化方法Recrystallise -solanine from EtOH, 85% aqueous EtOH, MeOH or aqueous MeOH as dihydrate m 276-278o. It solubility in H2O is 25mg/L and 5% in pyridine, but it is very soluble in Et2O and CHCl3. The hydrochloride is gummy or amorphous but has been crystallised (m ~212o dec). It has insecticidal properties. [Kuhn et al. Chem Ber 88 1492 1955, Beilstein 21 III/IV 1402.]

補足説明

定義ChEBI: A glycoalkaloid poison found in species of the nightshade family (Solanaceae), such as the potato (Solanum tuberosum). It is a trisccharide derivative of solanidine [(22beta)-solanid-5-en-3beta-ol].