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α-Solanine

α-Solanine structure

α-Solanine 

structure
  • CAS No:

    20562-02-1

  • Formula:

    C45H73NO15

  • Chemical Name:

    α-Solanine

  • Synonyms:

    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;Solanidane,β-D-galactopyranoside deriv.;1H-Naphth[2′,1′:4,5]indeno[1,2-b]indolizine,β-D-galactopyranoside deriv.;(3β)-Solanid-5-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranoside;α-Solanin;125-97-3;11017-45-1;32242-09-4;73681-48-8

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

White solid


A mixture of alpha-chaconine and alpha-solanine, found in SOLANACEAE plants.

α-Solanine Basic Attributes

868.06

868.06

243-879-8

15XXN7Q45T

DTXSID9030707

SLENDER NEEDLES FROM 85% ALC

29399990

Characteristics

240.69000

5.67

1.4±0.1 g/cm3

285 °C (decomp)

780.78°C (rough estimate)

1.631

26.04mg/L(15 ºC)

−20°C

PK @ 15 °C= 6.66; K= 2.2X10-7

BROWNS AND SINTERS ABOUT 190 °C; DECOMP ABOUT 285 °C

Safety Information

III

6.1(b)

1544

3

22

1-25-45-24/25

WF0250000

Xn

H302

A 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)]

|Warning|H302 (97.62%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 42 companies from 2 notifications to the ECHA C&L Inventory.

Toxicity

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.

Drug Information

5(?). 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG, BETWEEN 7 DROPS AND 1 TEASPOON FOR 70 KG PERSON (150 LB).

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.

Solanine

α-Solanine Use and Manufacturing

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.

HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIC SEPARATION OF POTATO GLYCOALKALOIDS USING A RADIALLY COMPRESSED AMINO COLUMN.|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).

AN ENZYME-LINKED IMMUNOSORBENT ASSAY OF BLOOD SERUM FOR TOTAL GLYCOALKALOIDS IN POTATO TUBERS.

Food Contaminant -> NATURALLY_OCCURRING_TOXICANT; -> JECFA Functional Classes

Food Contaminant -> NATURALLY_OCCURRING_TOXICANT;

Computed Properties

Molecular Weight:868.1
XLogP3:1.8
Hydrogen Bond Donor Count:9
Hydrogen Bond Acceptor Count:16
Rotatable Bond Count:8
Exact Mass:867.49802062
Monoisotopic Mass:867.49802062
Topological Polar Surface Area:241
Heavy Atom Count:61
Complexity:1590
Defined Atom Stereocenter Count:26
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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