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    • Penta International Corporation
      Chemistry innovation
      At Penta, our products and services help businesses do business better.
      For over 30 years, Penta Manufacturing Company has played a growing role in worldwide chemistry innovations and applications. As an industry leader, Penta continues to pioneer chemistry-based solutions for practically every area of commerce. Our products and expertise have helped fuel technical advances in dozens of commercial applications including flavoring, coloring, fragrances and chemical processes.
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      19-45000 SPILANTHOL, Kosher
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(2E,6Z,8E)-N-(2-methylpropyl)deca-2,6,8-trienamide (Click)
CAS Number: 25394-57-4
FDA UNII: 4W9L3S4856
FEMA Number: 4668
XlogP3-AA: 3.60 (est)
Molecular Weight: 221.34351000
Formula: C14 H23 N O
NMR Predictor: Predict
EFSA/JECFA Comments: Synonym: (2E,6Z,8E)-N-(2-Methylpropyl)-2,6,8-decatrienamide. Mixture of isomers: 74.007 % (2E,6Z,8E)-, 16.669 % (2E,6E,8E)-, 5.759 % (2E,6E,8Z)-, 0.884 % (2Z,6Z,8E)-, 0.334 % (2E,6E,8E)-, 0.764 % (2Z,6Z,8Z)-isomer, 1.553 % other isomers.
Category: flavor enhancers, flavoring agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
Read: Under the conditions of intended use - New developments in the FEMA GRAS program and the safety assessment of flavor ingredients
Read: A GRAS assessment program for flavor ingredients
Read: Sensory testing for flavorings with modifying properties. Food Technology
Read: Criteria for the safety evaluation of flavoring substances
Read: A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils
Read: FEMA Expert Panel: 30 Years of safety evaluation for the flavor industry
Read: Consumption ratio and food predominance of flavoring materials
JECFA Food Flavoring: 2077  (2E,6E/Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide
Flavis Number: 16.121 (Old)
EU SANCO Food Flavourings: 16.121  spilanthol

FEMA Number: 4668  (2E,6E/Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide
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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 mm/Hg @ 25.00 °C. (est)
Flash Point: 453.00 °F. TCC ( 234.00 °C. ) (est)
logP (o/w): 3.284 (est)
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Organoleptic Properties:
Odor Type: fruity
Odor Description:
Taste Description:
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Cosmetic Information:
None found
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BOC Sciences
LANOL-2,6,8-Decatrienamide, N-(2-methylpropyl)-, (E,E,Z)- (9CI)
For experimental / research use only.
J&K Chemical
For experimental / research use only.
Penta International
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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
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50  4378 mg/kg
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 17, Pg. 277, 1970.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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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
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
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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
Chemicalize.org: Calculate predicted properties
EPA ACToR: Toxicology Data
National Institute of Allergy and Infectious Diseases: Data
Chemidplus: 0025394574
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NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5353001
Pubchem (sid): 134997240
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS): View
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
None Found
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Potential Uses:
 chewing gum 
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Natural Occurrence in: note
 acmella ciliata
GRIN Trop Picture
 spilanthes acmella extracts
GRIN Trop Picture
 spilanthes acmella murr. extracts
GRIN Trop Picture
 spilanthes calva
GRIN Trop Picture
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2,6,8-decatrienamide, N-(2-methylpropyl)-, (2E,6Z,8E)-
(2E,6E/Z,8E)-N-(2-methyl propyl)-2,6,8-decatrienamide
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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 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].
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Picture of molecule
Soluble in:
 water, 13.32 mg/L @ 25 °C (est)
Insoluble in:
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