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solanidine
solanid-5-en-3-ol, (3-beta)- (9CI)

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CAS Number: 80-78-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-309-5
FDA UNII: W7801OHM8B
Nikkaji Web:J4.255B
Beilstein Number:0045370
MDL:MFCD00056839
XlogP3-AA:6.10 (est)
Molecular Weight:397.64591000
Formula:C27 H43 N O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 218.50 °C. @ 760.00 mm Hg
Boiling Point: 503.10 °C. @ 760.00 mm Hg (est)
Flash Point: 434.00 °F. TCC ( 223.50 °C. ) (est)
logP (o/w): 7.100 (est)
Soluble in:
 water, 0.01976 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
SOLANIDINE 95%
ExtraSynthese
For experimental / research use only.
Solanidine (HPLC) ≥99%
Sigma-Aldrich: Sigma
For experimental / research use only.
Solanidine ≥97.0% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
parenteral-frog LDLo 30 mg/kg
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 26, Pg. 88, 1890.

Dermal Toxicity:
subcutaneous-guinea pig LDLo 130 mg/kg
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 26, Pg. 88, 1890.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for solanidine usage levels up to:
 not for fragrance use.
 
Recommendation for solanidine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :65727
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0000080784
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):65727
Pubchem (sid):135023174
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C06543
HMDB (The Human Metabolome Database):HMDB03236
FooDB:FDB012098
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 cayenne fruit
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 eggplant fruit
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 pepper bell pepper fruit
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 pepper bell pepper leaf
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 potato fruit
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 potato leaf
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 potato plant
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 potato root
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 potato sprout
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 potato stem
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 potato tissue culture
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 potato tuber
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 tomato fruit
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Synonyms:
 solanid-5-en-3-beta-ol
3-beta-solanid-5-en-3-ol
 solanid-5-en-3-ol, (3-beta)- (9CI)
 solanid-5-en-3-ol, (3beta)- (9CI)
 solanid-5-en-3beta-ol (8CI)
22R,25S-solanidanine
 solanidin
22R,25S-solanidine
 solatubin
 solatubine
 

Articles:

PubMed:[Determination of alpha-solanine, alpha-chaconine and solanidine in plasma and urine by ultra-performance liquid chromatography-triple quadrupole mass spectrometry].
PubMed:Ultrasonic extraction of steroidal alkaloids from potato peel waste.
PubMed:Anticancer and multidrug resistance-reversal effects of solanidine analogs synthetized from pregnadienolone acetate.
PubMed:Allelic variation in genes contributing to glycoalkaloid biosynthesis in a diploid interspecific population of potato.
PubMed:Sequence diversity in coding regions of candidate genes in the glycoalkaloid biosynthetic pathway of wild potato species.
PubMed:Solanidine isolation from Solanum tuberosum by centrifugal partition chromatography.
PubMed:Use of potentiometric detection in (ultra) high performance liquid chromatography and modelling with adsorption/desorption binding kinetics.
PubMed:Anti-inflammatory properties of potato glycoalkaloids in stimulated Jurkat and Raw 264.7 mouse macrophages.
PubMed:FT-ICR/MS and GC-EI/MS metabolomics networking unravels global potato sprout's responses to Rhizoctonia solani infection.
PubMed:Induction of potato steroidal glycoalkaloid biosynthetic pathway by overexpression of cDNA encoding primary metabolism HMG-CoA reductase and squalene synthase.
PubMed:Effects of auxins on the production of steroidal alkaloids in rapidly proliferating tissue and cell cultures of Solanum lyratum.
PubMed:The effects of feeding diets containing potato protein concentrate on reproductive performance of rats and quality of the offspring.
PubMed:Antiproliferative effects of some novel synthetic solanidine analogs on HL-60 human leukemia cells in vitro.
PubMed:Linkage analysis of a rare alkaloid present in a tetraploid potato with Solanum chacoense background.
PubMed:Ingestion of false hellebore plants can cross-react with a digoxin clinical chemistry assay.
PubMed:Two 22S-solanidine-type steroidal alkaloids from Fritillaria anhuiensis.
PubMed:A QTL that confers resistance to Colorado potato beetle (Leptinotarsa decemlineata [Say]) in tetraploid potato populations segregating for leptine.
PubMed:Degradation of the potato glycoalkaloids--alpha-solanine and alpha-chaconine in groundwater.
PubMed:Distribution of glycoalkaloids in potato tubers of 59 accessions of two wild and five cultivated Solanum species.
PubMed:Potato glycoalkaloids in soil-optimising liquid chromatography-time-of-flight mass spectrometry for quantitative studies.
PubMed:Steroidal glycoalkaloids from the berries of Solanum distichum.
PubMed:Identification and characterization of several dietary alkaloids as weak inhibitors of hedgehog signaling.
PubMed:Potato steroidal glycoalkaloid levels and the expression of key isoprenoid metabolic genes.
PubMed:CHIH-DFT determination of the molecular structure and IR and UV spectra of solanidine.
PubMed:The primary in vivo steroidal alkaloid glucosyltransferase from potato.
PubMed:Liquid-liquid systems for acid hydrolysis of glycoalkaloids from Solanum tuberosum L. tuber sprouts and solanidine extraction.
PubMed:A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum.
PubMed:Structure-function relationship for saponin effects on cell cycle arrest and apoptosis in the human 1547 osteosarcoma cells: a molecular modelling approach of natural molecules structurally close to diosgenin.
PubMed:Effects of steroidal glycoalkaloids from potatoes (Solanum tuberosum) on in vitro bovine embryo development.
PubMed:Glycoalkaloid aglycone accumulations associated with infection by Clavibacter michiganensis ssp. sepedonicus in potato species Solanum acaule and Solanum tuberosum and their interspecific somatic hybrids.
PubMed:Enrichment of the glycoalkaloids alpha-solanine and alpha-chaconine from potato juice by adsorptive bubble separation using a pH gradient.
PubMed:Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.
PubMed:Development and optimisation of biosensors based on pH-sensitive field effect transistors and cholinesterases for sensitive detection of solanaceous glycoalkaloids.
PubMed:Solanidine hydrolytic extraction and separation from the potato (Solanum tuberosum L.) vines by using solid-liquid-liquid systems.
PubMed:Cyclopamine and jervine in embryonic rat tongue cultures demonstrate a role for Shh signaling in taste papilla development and patterning: fungiform papillae double in number and form in novel locations in dorsal lingual epithelium.
PubMed:Monitoring changes in anthocyanin and steroid alkaloid glycoside content in lines of transgenic potato plants using liquid chromatography/mass spectrometry.
PubMed:Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice.
PubMed:Sonic hedgehog activates mesenchymal Gli1 expression during prostate ductal bud formation.
PubMed:Determination of glycoalkaloids and relative aglycones by nonaqueous capillary electrophoresis coupled with electrospray ionization-ion trap mass spectrometry.
PubMed:Chemical toxins and body defences.
PubMed:A novel enzyme biosensor for steroidal glycoalkaloids detection based on pH-sensitive field effect transistors.
PubMed:Effect of light exposure on the glycoalkaloid content of Solanum phureja tubers.
PubMed:Non-aqueous capillary electrophoresis with diode array and electrospray mass spectrometric detection for the analysis of selected steroidal alkaloids in plant extracts.
PubMed:Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells.
PubMed:Membrane disruption and enzyme inhibition by naturally-occurring and modified chacotriose-containing Solanum steroidal glycoalkaloids.
PubMed:A capillary electrophoresis laser-induced fluorescence method for analysis of potato glycoalkaloids based on a solution-phase immunoassay. 2. Performance evaluation.
PubMed:Induction of steroidal hydroxylase activity by plant defence compounds in the filamentous fungus Cochliobolus lunatus
PubMed:Photo-induced synthesis of tomatidenol-based glycoalkaloids in Solanum phureja tubers.
PubMed:A capillary electrophoresis laser-induced fluorescence method for analysis of potato glycoalkaloids based on a solution-phase immunoassay. 1. Separation and quantification of immunoassay products.
PubMed:Simultaneous determination of seven major isosteroidal alkaloids in bulbs of Fritillaria by gas chromatography.
PubMed:Determination of solanidine- and tomatidine-type glycoalkaloid aglycons by gas Chromatography/Mass spectrometry.
PubMed:Inhibition of Trypanosoma cruzi growth in vitro by Solanum alkaloids: a comparison with ketoconazole.
PubMed:Substrate-based inhibitors of the (S)-adenosyl-L-methionine:delta24(25)- to delta24(28)-sterol methyl transferase from Saccharomyces cerevisiae.
PubMed:Cloning and expression of solanidine UDP-glucose glucosyltransferase from potato.
PubMed:Synthesis of gamma-chaconine and gamma-solanine are catalyzed in potato by two separate glycosyltransferases: UDP-glucose:solanidine glucosyltransferase and UDP-galactose:solanidine galactosyltransferase.
PubMed:UDP-glucose:solasodine glucosyltransferase from eggplant (Solanum melongena L.) leaves: partial purification and characterization.
PubMed:Inhibition of human plasma and serum butyrylcholinesterase (EC 3.1.1.8) by alpha-chaconine and alpha-solanine.
PubMed:Feeding of potato, tomato and eggplant alkaloids affects food consumption and body and liver weights in mice.
PubMed:Induction of terata in hamsters by solanidane alkaloids derived from Solanum tuberosum.
PubMed:Comparison of high- and low-energy collision-induced dissociation tandem mass spectrometry in the analysis of glycoalkaloids and their aglycons.
PubMed:A preliminary assessment of the toxic and mutagenic potential of steroidal alkaloids in transgenic mice.
PubMed:Steroidal alkaloid toxicity to fish embryos.
PubMed:Dual specificity of sterol-mediated glycoalkaloid induced membrane disruption.
PubMed:Absence of genotoxicity of potato alkaloids alpha-chaconine, alpha-solanine and solanidine in the Ames Salmonella and adult and foetal erythrocyte micronucleus assays.
PubMed:Interspecific hybridization between the cultivated potato Solanum tuberosum subspecies tuberosum L. and the wild species S. circaeifolium subsp. circaeifolium Bitter exhibiting resistance to Phytophthora infestans (Mont.) de Bary and Globodera pallida (Stone) Behrens : 2. Sexual hybrids.
PubMed:Partial amino acid sequence of potato solanidine UDP-glucose glucosyltransferase purified by new anion-exchange and size exclusion media.
PubMed:Intramolecular relationships in cholinesterases revealed by oocyte expression of site-directed and natural variants of human BCHE.
PubMed:Determination of potato glycoalkaloids and their aglycone in blood serum by high-performance liquid chromatography. Application to pharmacokinetic studies in humans.
PubMed:Developmental toxicology of potato alkaloids in the frog embryo teratogenesis assay--Xenopus (FETAX).
PubMed:Hepatic ornithine decarboxylase induction by potato glycoalkaloids in rats.
PubMed:Aspartate-70 to glycine substitution confers resistance to naturally occurring and synthetic anionic-site ligands on in-ovo produced human butyrylcholinesterase.
PubMed:Spirosolane-containing Solanum species and induction of congenital craniofacial malformations.
PubMed:Use of ion-pairing reversed-phase liquid chromatography in separation of solanidine and solasodine.
PubMed:Pathology in hamsters administered Solanum plant species that contain steroidal alkaloids.
PubMed:Potato steroidal alkaloids and neural tube defects: serum concentrations fail to demonstrate a causal relation.
PubMed:The inactivation of herpes simplex virus by some Solanaceae glycoalkaloids.
PubMed:Measurement of potato steroidal alkaloids in human serum and saliva by radioimmunoassay.
PubMed:Solanidine is present in sera of healthy individuals and in amounts dependent on their dietary potato consumption.
PubMed:Neural-tube defects produced in Syrian hamsters by potato glycoalkaloids.
PubMed:Determination of solanidine in human plasma by radioimmunoassay.
PubMed:Kinetics and retention of solanidine in man.
PubMed:Analysis of potato glycoalkaloids by gas-liquid chromatography of alkaloid components.
PubMed:Potato glycoalkaloids.
PubMed:[Nature and mechanism of action of the solanidine glycosides solanine and chaconine on biological objects].
PubMed:An outbreak of suspected solanine poisoning in schoolboys: Examinations of criteria of solanine poisoning.
PubMed:Analysis of mixtures of solanidine and demissidine glycoalkaloids containing identical carbohydrate units.
PubMed:[Determination of the solanine-chaconine ratio in potato sprouts and tubers (author's transl)].
PubMed:Positive inotropic action of Solanaceae glycoalkaloids.
PubMed:A novel pathway for the synthesis of solanidine in the isolated chloroplast from greening potatoes.
PubMed:High-pressure liquid chromatography of steroidal alkaloids.
PubMed:Excretion, distribution and metabolic fate of 3H-alpha-chaconine.
PubMed:[Determination of solanidine by the extraction-photometric method].
PubMed:Synthetic studies in steroidal alkaloids and sapogenins. VII. Synthesis of solanidine.
PubMed:[On the biosynthesis of steroid derivatives in the plant kingdom. 8. Biogenesis of solanidine from cholesterol].
PubMed:The microbial hydroxylation of solanidine and the mass spectrometric studies of some hydroxylated solanidines.
PubMed:[Solanum alkaloids. LIV. Synthesis of solanidine and 22-iso-solanidine from tomatid-5-ene-3-beta-ol].
PubMed:[SEPARATION OF SOLANINE, CHACONINE AND SOLANIDINE BY THIN LAYER CHROMATOGRAPHY].
PubMed:Differential inhibition of the serum cholinesterase phenotypes by solanine and solanidine.
PubMed:[Synthesis of solanidine from demissidine].
PubMed:The occurrence and distribution of free alkaloid solanidine in netted gem potatoes.
 
Notes:
derivative of diosgenin that can rearrange to solanine. Alkaloid from potato (Solanum tuberosum). Glycosides, (esp. Solanines and chaconine) are trace toxic constits. of potato tubers (esp. greened tubers), and interbreeding of potatoes with wild strains may increase their concn. or introduce other more toxic, solanidine glycosides Solanidine is a steroidal alkaloid, and its glycosides have been reported to have caused poisoning in man and animals. Solanidine is present in sera of healthy individuals and in amounts dependent on their dietary potato consumption. (PMID: 4007882)
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