spilanthol

(2E,6E/Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide

CAS: 25394-57-4 C14 H23 N O MW: 221.34351000 fruity salty

Identification

Namespilanthol
IUPAC(2E,6Z,8E)-N-(2-methylpropyl)deca-2,6,8-trienamide
CAS Number25394-57-4
FDA UNII4W9L3S4856
Molecular FormulaC14 H23 N O
Molecular Weight221.34351000

Regulatory

JECFA Food Flavoring2077 (2E,6E/Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide
DG SANTE Food Flavourings16.121 spilanthol
FEMA Number4668
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)25394-57-4 ; (2E,6Z,8E)-N-(2-METHYLPROPYL)-2,6,8-DECATRIENAMIDE

Physical Properties

Appearance colorless to yellowish brown clear liquid to solid (est)
Assay 74.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 0.94520 to 0.94680 @ 25.00 °C.
Pounds per Gallon - (est). 7.865 to 7.878
Refractive Index 1.49110 to 1.54110 @ 20.00 °C.
Boiling Point 384.00 to 385.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure 0.000004 mmHg @ 25.00 °C. (est)
Flash Point 453.00 °F. TCC ( 234.00 °C. ) (est)
logP (o/w) 3.284 (est)
Soluble in alcohol

Organoleptic Properties

Odor Description at 100.00 %.
Taste Description salty

Safety Information

Oral/Parenteral Toxicityoral-mouse LD50 4378 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'BEHAVIORAL: TREMOR\nBEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)']

Safety in Use

Categoryflavor enhancers, flavoring agents
Recommendation for spilanthol usage levels up tonot for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU)24.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)670 (μg/person/day)
Threshold of Concern90 (μg/person/day)
Structure ClassIII
baked goods-
beverages(nonalcoholic)15.00000
beverages(alcoholic)12.50000
breakfast cereal15.00000
cheese-
chewing gum100.00000
condiments / relishes5.00000
confectionery froastings35.00000
egg products-
fats / oils-
fish products5.00000
frozen dairy12.50000
fruit ices12.50000
gelatins / puddings12.50000
granulated sugar-
gravies-
hard candy115.00000
imitation dairy-
instant coffee / tea-
jams / jellies12.50000
meat products-
milk products-
nut products-
other grains-
poultry-
processed fruits2.50000
processed vegetables-
reconstituted vegetables-
seasonings / flavors12.50000
snack foods25.00000
soft candy115.00000
soups7.50000
sugar substitutes-
sweet sauces-
Dairy products, excluding products of category 02.0 (01.0)1.25000
Fats and oils, and fat emulsions (type water-in-oil) (02.0)-
Edible ices, including sherbet and sorbet (03.0)1.25000
Processed fruit (04.1)0.25000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)10.00000
Chewing gum (05.3)-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)1.00000
Bakery wares (07.0)-
Meat and meat products, including poultry and game (08.0)-
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)0.50000
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)0.75000
Foodstuffs intended for particular nutritional uses (13.0)-
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)0.50000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)1.00000
Ready-to-eat savouries (15.0)0.50000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)1.00000

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Potential Uses

chewing gum FR mint

Natural Occurrence

acmella ciliata spilanthes acmella extracts spilanthes acmella murr. extracts spilanthes calva

Synonyms

affinin (2E,6Z,8E)-N-iso butyl-2,6,8-decatrienamid (2E,6Z,8E)-N-iso butyl-2,6,8-decatrienamide N-iso butyl-2(E),6(Z),8(E)-decatrienamide N-iso butyl-2E-decenamide N-iso butyldeca-trans-2-cis-6-trans-8-trienamide 2,6,8- decatrienamide, N-(2-methylpropyl)-, (2E,6Z,8E)- (2E,6E/Z,8E)-N-(2- methyl propyl)-2,6,8-decatrienamide (2E,6E/Z,8E)-N-(2- methylpropyl)-2,6,8-decatrienamide (2E,6Z,8E)-N-(2- methylpropyl)deca-2,6,8-trienamide Google Patents: SYNTHETIC SPILANTHOL AND USE THEREOF PubMed: In vitro clonal propagation and genetic fidelity of the regenerants of Spilanthes calva DC. using RAPD and ISSR marker. Google Books: Flavour science: recent advances and trends Leffingwell & Associates: Flavor Properties of FEMA GRAS List 25 flavor chemicals Google Patents: Use of an Acmella Oleracea Extract for the Botox-Like Effect Thereof in an Anti-Wrinkle Cosmetic Composition Google Books: Wine Chemistry and Biochemistry Google Books: Chemistry and technology of flavors and fragrances Google Books: Flavours and fragrances: chemistry, bioprocessing and sustainability Google Books: Chemistry and technology of flavors and fragrances PubMed: Antinociceptive effects of ethanolic extract from the flowers of Acmella oleracea (L.) R.K. Jansen in mice. PubMed: Skin penetration enhancing properties of the plant N-alkylamide spilanthol. PubMed: The traditional medicine Spilanthes acmella, and the alkylamides spilanthol and undeca-2E-ene-8,10-diynoic acid isobutylamide, demonstrate in vitro and in vivo antimalarial activity. PubMed: Gustatory, trigeminal, and olfactory aspects of nicotine intake in three mouse strains. PubMed: Evaluation of nutrient uptake and physical parameters on cell biomass growth and production of spilanthol in suspension cultures of Spilanthes acmella Murr. PubMed: Bioactivity of compounds from Acmella oleracea against Tuta absoluta (Meyrick) (Lepidoptera: Gelechiidae) and selectivity to two non-target species. PubMed: Lifting properties of the alkamide fraction from the fruit husks of Zanthoxylum bungeanum. PubMed: A new discriminative criterion for the development of Franz diffusion tests for transdermal pharmaceuticals. PubMed: A validated liquid chromatography-electrospray ionization-mass spectrometry method for quantification of spilanthol in Spilanthes acmella (L.) Murr. PubMed: LC-MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol. PubMed: Transdermal behaviour of the N-alkylamide spilanthol (affinin) from Spilanthes acmella (Compositae) extracts. PubMed: Anti-inflammatory effects of ethanolic extract and alkamides-derived from Heliopsis longipes roots. PubMed: Anti-inflammatory effect of spilanthol from Spilanthes acmella on murine macrophage by down-regulating LPS-induced inflammatory mediators. PubMed: Isolation and synthesis of acmellonate, a new unsaturated long chain 2-ketol ester from Spilanthes acmella. PubMed: Antifungal potential of Spilanthes calva after inoculation of Piriformospora indica. PubMed: Proposed mechanisms for the fragmentation of doubly allylic alkenamides (tingle compounds) by low energy collisional activation in a triple quadrupole mass spectrometer. PubMed: Bioactive N-isobutylamides from the flower buds of Spilanthes acmella. PubMed: [Effect of spilanthol (extracted from jambu) on action potentials. Electric recordings in atrial fiber]. PubMed: [Effect of spilanthol (extracted from jambu) on the electrical activity of the rabbit heart. The experimental electrocardiogram].