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spilanthol

Spilanthol is a natural amide found in Spilanthes acmella extracts with a fruity odor and salty flavor, used primarily as a flavor enhancer in food products.
Chemical Structure

General Material Description

Spilanthol is a naturally occurring alkamide with the molecular formula C14H23NO. It is known chemically as (2E,6Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide and has synonyms including affinin and various stereoisomeric names reflecting its structure. This compound commonly appears in botanical sources such as Spilanthes acmella, often termed the 'toothache plant,' from which it is extracted. Recognized for its fruity odor and distinctive salty flavor, spilanthol is a colorless to pale yellow oily liquid that contributes sensory attributes to food products. Its chemical information is cataloged in controlled-vocabulary databases such as PubChem. The compound is primarily sourced through natural extraction from plant material utilized traditionally in various cultural preparations.

Occurrence, Applicability & Potential Uses

Spilanthol naturally occurs in species of the genus Spilanthes, including Spilanthes acmella, Spilanthes calva, and related plant extracts. It is a key constituent credited for the distinctive sensory profile of these botanicals. Its applications encompass use as a flavor enhancer in food products, compliant with standards such as FEMA (US), which classifies it under FEMA number 4668 for use in beverages, confectionery, chewing gum, and other consumables. Spilanthol is valued in food formulation for imparting a subtle fruity odor and a salty taste, with reported uses especially in chewing gums where it enhances sensory impact. These applications reflect its functional roles as both a flavoring agent and modulator.

Physico-Chemical Properties Summary

Spilanthol exhibits physical properties that influence its handling and formulation. It is an oily liquid with a specific gravity ranging approximately from 0.9452 to 0.9468 at 25 °C and a refractive index between 1.4911 and 1.5411 at 20 °C. Its boiling point lies between 384 and 385 °C at standard atmospheric pressure (760 mm Hg). The compound's vapor pressure is notably low at 4.0 × 10−6 mmHg at 25 °C, indicating low volatility under ambient conditions. It has moderate lipophilicity with an estimated logP value around 3.3, suggesting preferential solubility in nonpolar solvents; this is consistent with its solubility profile, being soluble in alcohol and sparingly soluble in water at approximately 13.32 mg/L at 25 °C. The flash point is approximately 453 °F, which translates to about 234 °C, indicating relative thermal stability. These characteristics affect its incorporation into flavor formulations and stability considerations.

FAQ

What is spilanthol and where is it found naturally?
Spilanthol is a natural alkamide characterized chemically as (2E,6Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide. It occurs primarily in plant species within the genus Spilanthes, notably Spilanthes acmella and Spilanthes calva. These plants are known for their use in traditional herbal preparations, with spilanthol contributing to their distinctive sensory properties. The compound imparts fruity odor and salty taste qualities, making it significant in flavor science. Its presence in these botanical sources arises as part of their secondary metabolite profile.
How is spilanthol used in flavor applications and what standards regulate its use?
Spilanthol serves predominantly as a flavor enhancer and flavoring agent in various food products, including nonalcoholic and alcoholic beverages, confectionery, chewing gum, and processed fruit preparations. Regulatory standards such as FEMA (Flavor and Extract Manufacturers Association of the United States) recognize it under FEMA number 4668, permitting its incorporation under specified usage levels. Its applications are supported by safety evaluations, allowing controlled uses in food with defined maximum concentration limits to ensure consumer safety. These guidelines assist formulators in leveraging its sensory attributes effectively while maintaining compliance.
What safety information and regulatory reviews exist for spilanthol?
Spilanthol has undergone safety assessment by several authorities, including FEMA (US) and EFSA (European Food Safety Authority). The compound presents no classified hazards under OSHA's Globally Harmonized System (GHS) regulations and exhibits relatively low acute toxicity based on animal studies. EFSA's Flavouring Group Evaluation 303 (FGE.303) provides scientific opinions on its safety, including usage limitations in food products. Maximized Survey-derived Daily Intakes (MSDI) and Threshold of Concern levels have been established to guide safe exposure. These comprehensive evaluations offer reassurance regarding its use as a flavoring substance within regulated limits.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

(2E,6Z,8E)-N-(2-methylpropyl)deca-2,6,8-trienamide
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5353001
Pubchem (sid):134997240
Publications by Google Patents
SYNTHETIC SPILANTHOL AND USE THEREOF
Use of an Acmella Oleracea Extract for the Botox-Like Effect Thereof in an Anti-Wrinkle Cosmetic Composition
Publications by PubMed
In vitro clonal propagation and genetic fidelity of the regenerants of Spilanthes calva DC. using RAPD and ISSR marker.
Antinociceptive effects of ethanolic extract from the flowers of Acmella oleracea (L.) R.K. Jansen in mice.
Skin penetration enhancing properties of the plant N-alkylamide spilanthol.
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.
Gustatory, trigeminal, and olfactory aspects of nicotine intake in three mouse strains.
Evaluation of nutrient uptake and physical parameters on cell biomass growth and production of spilanthol in suspension cultures of Spilanthes acmella Murr.
Bioactivity of compounds from Acmella oleracea against Tuta absoluta (Meyrick) (Lepidoptera: Gelechiidae) and selectivity to two non-target species.
Lifting properties of the alkamide fraction from the fruit husks of Zanthoxylum bungeanum.
A new discriminative criterion for the development of Franz diffusion tests for transdermal pharmaceuticals.
A validated liquid chromatography-electrospray ionization-mass spectrometry method for quantification of spilanthol in Spilanthes acmella (L.) Murr.
LC-MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol.
Transdermal behaviour of the N-alkylamide spilanthol (affinin) from Spilanthes acmella (Compositae) extracts.
Anti-inflammatory effects of ethanolic extract and alkamides-derived from Heliopsis longipes roots.
Anti-inflammatory effect of spilanthol from Spilanthes acmella on murine macrophage by down-regulating LPS-induced inflammatory mediators.
Isolation and synthesis of acmellonate, a new unsaturated long chain 2-ketol ester from Spilanthes acmella.
Antifungal potential of Spilanthes calva after inoculation of Piriformospora indica.
Proposed mechanisms for the fragmentation of doubly allylic alkenamides (tingle compounds) by low energy collisional activation in a triple quadrupole mass spectrometer.
Bioactive N-isobutylamides from the flower buds of Spilanthes acmella.
[Effect of spilanthol (extracted from jambu) on action potentials. Electric recordings in atrial fiber].
[Effect of spilanthol (extracted from jambu) on the electrical activity of the rabbit heart. The experimental electrocardiogram].
Publications by Google Books
Flavour science: recent advances and trends
Wine Chemistry and Biochemistry
Chemistry and technology of flavors and fragrances
Flavours and fragrances: chemistry, bioprocessing and sustainability
Chemistry and technology of flavors and fragrances
Publications by Leffingwell & Associates
Flavor Properties of FEMA GRAS List 25 flavor chemicals

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
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

General Material Information

Preferred name spilanthol
Trivial Name Spilanthol
Short Description (2E,6E/Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide
Formula C14 H23 N O
CAS Number 25394-57-4
Deleted CAS Number 504-47-2
FEMA Number 4668
Flavis Number 16.121
FDA UNII 4W9L3S4856
xLogP3-AA 3.60 (est)
NMR Predictor External link
JECFA Food Flavoring 2077 (2E,6E/Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 25394-57-4 ; (2E,6Z,8E)-N-(2-METHYLPROPYL)-2,6,8-DECATRIENAMIDE
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
  • (2E,6Z,8E)-N-(2-methylpropyl)deca-2,6,8-trienamide
  • 2,6,8-Decatrienamide, N-(2-methylpropyl)-, (2E,6Z,8E)-
  • 2,6,8-Decatrienamide, N-isobutyl-, (E,E,Z)-
  • 2,6,8-Decatrienamide, N-(2-methylpropyl)-, (E,E,Z)-
  • (2E,6Z,8E)-N-(2-Methylpropyl)-2,6,8-decatrienamide
  • N-Isobutyldeca-trans-2,cis-6,trans-8-trienamide
  • 2E,6Z,8E-Decatrienoic acid N-isobutylamide

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 221.34350585938
Specific gravity @ 25 °C
Pounds per Gallon 7.865 to 7.878
Refractive Index 1.4911 to 1.5411 @ 20 °C
Boiling Point 384 to 385°C @ 760 mm Hg
Vapor Pressure 4.0E-6 mmHg @ 25 °C
Flash Point TCC Value 234 °C TCC
logP (o/w) 3.284 est
Solubility
alcohol Yes
water, 13.32 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Fruity
fruity
General comment At 100.00 %. fruity
Flavor Type: Salty
salty
General comment Salty

Occurrences

Potential Uses

Applications
Odor purposes Mint
Other purposes Chewing gum

Safety Information

Safety information

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:
oral-mouse LD50 4378 mg/kg
BEHAVIORAL: TREMOR BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 17, Pg. 277, 1970.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

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
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 25
Click here to view publication 25
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): 15.0000030.00000
beverages(alcoholic): 12.5000030.00000
breakfast cereal: 15.0000030.00000
cheese: --
chewing gum: 100.00000250.00000
condiments / relishes: 5.0000015.00000
confectionery froastings: 35.0000075.00000
egg products: --
fats / oils: --
fish products: 5.0000015.00000
frozen dairy: 12.5000025.00000
fruit ices: 12.5000025.00000
gelatins / puddings: 12.5000020.00000
granulated sugar: --
gravies: --
hard candy: 115.00000175.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: 12.5000025.00000
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: 2.5000010.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 12.5000025.00000
snack foods: 25.0000050.00000
soft candy: 115.00000150.00000
soups: 7.5000015.00000
sugar substitutes: --
sweet sauces: --
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 1.250002.50000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): --
Edible ices, including sherbet and sorbet (03.0): 1.250002.50000
Processed fruit (04.1): 0.250001.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000017.50000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 1.000003.00000
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): 0.500001.50000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.750001.50000
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.500001.50000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 1.000003.00000
Ready-to-eat savouries (15.0): 0.500001.50000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 1.000003.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Scientific Opinion on Flavouring Group Evaluation 303 (FGE.303): Spilanthol from chemical group 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 303, Revision 1 (FGE.303Rev1): Spilanthol from chemical group 30
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5353001
National Institute of Allergy and Infectious Diseases:Data
(2E,6Z,8E)-N-(2-methylpropyl)deca-2,6,8-trienamide
Chemidplus:0025394574