spilanthol
(2E,6E/Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide
Identification
| Name | spilanthol |
| IUPAC | (2E,6Z,8E)-N-(2-methylpropyl)deca-2,6,8-trienamide |
| CAS Number | 25394-57-4 |
| FDA UNII | 4W9L3S4856 |
| Molecular Formula | C14 H23 N O |
| Molecular Weight | 221.34351000 |
Regulatory
| JECFA Food Flavoring | 2077 (2E,6E/Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide |
| DG SANTE Food Flavourings | 16.121 spilanthol |
| FEMA Number | 4668 |
| FDA | No 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 Toxicity | oral-mouse LD50 4378 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not 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
| Category | flavor enhancers, flavoring agents |
| Recommendation for spilanthol usage levels up to | not 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 Concern | 90 (μg/person/day) |
| Structure Class | III |
| baked goods | - |
| beverages(nonalcoholic) | 15.00000 |
| beverages(alcoholic) | 12.50000 |
| breakfast cereal | 15.00000 |
| cheese | - |
| chewing gum | 100.00000 |
| condiments / relishes | 5.00000 |
| confectionery froastings | 35.00000 |
| egg products | - |
| fats / oils | - |
| fish products | 5.00000 |
| frozen dairy | 12.50000 |
| fruit ices | 12.50000 |
| gelatins / puddings | 12.50000 |
| granulated sugar | - |
| gravies | - |
| hard candy | 115.00000 |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | 12.50000 |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | 2.50000 |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | 12.50000 |
| snack foods | 25.00000 |
| soft candy | 115.00000 |
| soups | 7.50000 |
| 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
Natural Occurrence
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].