alpha-Solanine

ChemicalBook > CAS DataBase List > alpha-Solanine

Product Name: alpha-Solanine
CAS No.: 20562-02-1
Chemical Name: alpha-Solanine
Synonyms: solanine;SOLATUNIN;α-Solanin;SOLATUNINE;a-Solanine;α-Solanine;ALPHA-SOLANIN;α-Solanine-RM;ALPHA-SOLANINE;α-Solanine ,99%
CBNumber: CB9696314
Molecular Formula: C45H73NO15
Formula Weight: 868.07
MOL File: 20562-02-1.mol

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alpha-Solanine Property

Melting point:: 285℃ (dec.)
Boiling point:: 780.78°C (rough estimate)
Density: 1.40±0.1 g/cm3 (20 ºC 760 Torr)
refractive index: 1.5280 (estimate)
storage temp.: −20°C
solubility: Methanol (Slightly, Heated), Pyridine (Slightly, Sonicated), Water (Slightly, Heated)
form: Solid
pka: 6.66(at 15℃)
color: White to Off-White
Water Solubility: 26.04mg/L(15 ºC)
Merck: 13,8779
BRN: 77607
InChIKey: ZGVSETXHNHBTRK-MUEWWJAYNA-N
LogP: 5.670 (est)

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Safety

Hazard Codes: Xn
Risk Statements: 22
Safety Statements: 1-25-45-24/25
RIDADR: 1544
WGK Germany: 3
RTECS: WF0250000
F: 10
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29399990
Hazardous Substances Data: 20562-02-1(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: S3757
Product name: α-Solanine
Purity: from potato sprouts, ≥95%
Packaging: 5mg
Price: $152
Updated: 2024/03/01

Sigma-Aldrich

Product number: S3757
Product name: α-Solanine
Purity: from potato sprouts, ≥95%
Packaging: 10mg
Price: $227
Updated: 2024/03/01

Sigma-Aldrich

Product number: S3757
Product name: α-Solanine
Purity: from potato sprouts, ≥95%
Packaging: 50mg
Price: $766
Updated: 2024/03/01

Sigma-Aldrich

Product number: PHL80074
Product name: α-Solanine
Purity: phyproof Reference Substance
Packaging: 10mg
Price: $356
Updated: 2024/03/01

TRC

Product number: S676503
Product name: α-Solanine
Packaging: 2.5mg
Price: $200
Updated: 2021/12/16

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alpha-Solanine Chemical Properties,Usage,Production

Description

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]²⁰_D - 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.

Chemical Properties

White solid

Uses

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.

Definition

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].

benefits

It has been revealed that α-solanine possesses potential chemotherapeutic action against cancers in several organs, including lung, breast, esophagus, prostate, and liver, as well as acute lymphocytic leukemia. α-solanine also has potential anti-inflammatory properties[1].

General Description

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

Hazard

A poison.

Mechanism of action

In vitro studies have shown that alpha-Solanine's anti-cancer mechanism of action is induction of apoptosis, inhibition of cell proliferation and angiogenesis^[1]. It also regulates the nuclear factor-κB (NF-κB) signalling pathway in tumour cells and macrophages^[2].

Side effects

A small amount of α-solanine can cause common symptoms such as dizziness, nausea, abdominal pain, vomiting, and diarrhea. Excessive consumption of α-solanine can lead to convulsions, coma, and even death. Animal studies have shown that α-solanine can damage the reproductive system[1].

Toxicology

alpha-Solanine is the major glycoalkaloid in the potato plant and is toxic. Potatoes generally contain toxic alpha-Solanine when they have been left for a long period of time resulting in a greenish colouration of the surface. Poisoning after ingestion is manifested by nausea, vomiting, diarrhoea, abdominal pain, fever or below normal body temperature (hypothermia), slow pulse and/or respiration, and confusion.

Purification Methods

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.]

References

Desfosses.,lahresb., 2, 114 (1820)
Firbas., Monatsh., 10, 541 (1889)
Cazeneuve, Breteau., Compt. rend., 128,887 (1899)
Davis., Pharm. I., 15, 160 (1902)
Wittman., Monatsh., 26,445 (1905)
Colombano., Gazzetta, 38, 19 (1908)
Zemplen, Gerecs., Ber., 61,2294 (1928)
Schopf, Herrmann., ibid, 66, 298 (1933)
Oddo, Caronna., ibid, 67,446 (1934)

References

[1] Zhilong Chen. “α-Solanine Causes Cellular Dysfunction of Human Trophoblast Cells via Apoptosis and Autophagy.” Toxins (2021).

References

[1] MARYAM MOHSENIKIA . The protective and therapeutic effects of alpha-solanine on mice breast cancer[J]. European journal of pharmacology, 2013. DOI:10.1016/j.ejphar.2013.09.015.
[2] NAN WANG. Alpha-solanine inhibits endothelial inflammation via nuclear factor kappa B signaling pathway.[J]. Advances in Clinical and Experimental Medicine, 2023. DOI:10.17219/acem/158781.

alpha-Solanine Preparation Products And Raw materials

Raw materials

Preparation Products

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alpha-Solanine Suppliers

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20562-02-1, alpha-Solanine Related Search:

α-Sarcin α-sarcoglycan (D-7) N-OCTYL-BETA-D-GLUCOPYRANOSIDE 1,7-HEPTANEDIOL CONIINE, D/L-(RG) SOLANIDINE alpha-Solanine levopropylhexedrine Cyclopentylamine 2-CYCLOPENTYL-ETHYLAMINE Cyclopentamine iproheptine CYCLOPENTYL-METHYL-AMINE α-Chaconine solamargine Atropine SOLANINE S L-Hyoscyamine

SOLATUNIN

SOLATUNINE

beta-d-galactopyranoside,(3beta)-solanid-5-en-3-ylo-6-deoxy-alpha-l-mannopyra

POTATOGLYCOALKALOIDS

a-Solanine

alpha-solanin from potato sprouts

A-solanine from potato sprouts

alpha-SOLANINE tlc

A-SOLANINE WITH TLC

[Solanid-5-en-3β-yl]2-O-(6-deoxy-α-L-mannopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-galactopyranoside

3β-[2-O-(6-Deoxy-α-L-mannopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-galactopyranosyloxy]solanid-5-ene

Solanid-5-en-3β-yl 2-O-(6-deoxy-α-L-mannopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-galactopyranoside

α-Solanin

α-Solanidine,from Potao Sprouts

α-Solanine ,99%

alpha-Solanine froM potato sprouts, >=95%

ALPHA-SOLANIN

ALPHA-SOLANINE

nosyl-(1-2)-o-(beta-d-glucopyranosyl-(1-3))-

solanid-5-ene,3-beta-((o-6-deoxy-alpha-l-mannopyranosyl-(1-2)-o-(beta-d-glucop

solanid-5-ene,3-beta-((o-6-deoxy-alpha-l-mannopyranosyl-o-(beta-d-glucopyranos

solanine

yl-beta-d-galactopyranosyl)oxy)-

yranosyl-(1-3))-beta-d-galactopyranosyl)oxy)-

SOLANINE, ALPHA

β-D-Galactopyranoside, (3β)-solanid-5-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-

α-Solanine

ALPHA-SOLANINE USP/EP/BP

α-Solanine-RM

Azithromycin Impurity 66

20562-02-1

C45H73NO15

Complex Molecules

Chiral Building Blocks

Asymmetric Synthesis

Chiral Building Blocks

Complex Molecules

Alkaloids