EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

6-paradol
1-(4-hydroxy-3-methoxyphenyl)decan-3-one

Sponsors

Name:1-(4-hydroxy-3-methoxyphenyl)decan-3-one
CAS Number: 27113-22-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:248-228-1
FDA UNII:BO24ID7E9U
Nikkaji Web:J129.700G
Beilstein Number:1984119
XlogP3:3.80 (est)
Molecular Weight:278.39182000
Formula:C17 H26 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
Register name to be changed to 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone; CASrn: 27113-22-0 and EINECS: 248-228-1.
Category:cosmetic and flavor 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
JECFA Food Flavoring:2021 1-(4-hydroxy-3-methoxyphenyl)-decan-3-one
FLAVIS Number:07.234 (Old)
DG SANTE Food Flavourings:07.234 1-(4-hydroxy-3-methoxyphenyl)-decan-3-one
FEMA Number:4665 1-(4-hydroxy-3-methoxyphenyl)decan-3-one
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: 1-(4-HYDROXY-3-METHOXYPHENYL)DECAN-3-ONE
 
Physical Properties:
Appearance:white powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 31.00 to 33.00 °C. @ 760.00 mm Hg
Boiling Point: 406.00 to 408.00 °C. @ 760.00 mm Hg
Flash Point: 284.00 °F. TCC ( 140.00 °C. )
logP (o/w): 4.225 (est)
Soluble in:
 alcohol
 water, 3.802 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: spicy
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
BOC Sciences
For experimental / research use only.
Paradol >98%
Dalton Pharma Services
For experimental / research use only.
[6]-Paradol >95%
Jiangyin Healthway
6-Paradol
New functional food ingredients
Parchem
6-paradol
Symrise
SymRelief® S
Odor: characteristic
Use: SymRelief® S is a synergistic blend of 2 nature identical skin soothing ingredients: Dragosantol® 100 and [6]-paradol. Dragosantol® 100 is the synthetic bisabolol with the highest purity available in the market today; [6]-paradol is one of the pungent principles of ginger and grains of paradise (Afromum melegueta), synthetic and nature-identical. Each component synergistically contributes to SymRelief® S's broad skin soothing efficacy. SymRelief® S is perfect for sensitive skin as it significantly reduces redness and blotchiness already after 1 day of treatment.
Vigon International
SYMDECANOX HA
 
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:
intraperitoneal-mouse LD50 270 mg/kg
Journal of Toxicological Sciences. Vol. 16(Suppl.)

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: cosmetic and flavor agents
Recommendation for 6-paradol usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.012 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 420 (μg/person/day)
Threshold of Concern:540 (μg/person/day)
Structure Class: II
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: 24
 average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): 10.0000050.00000
beverages(alcoholic): 20.00000100.00000
breakfast cereal: --
cheese: --
chewing gum: 300.00000800.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: 80.00000250.00000
fish products: --
frozen dairy: 50.00000150.00000
fruit ices: --
gelatins / puddings: 50.00000150.00000
granulated sugar: --
gravies: --
hard candy: 50.00000150.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: 50.00000150.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 100.00000250.00000
snack foods: 20.0000050.00000
soft candy: 80.00000200.00000
soups: 20.00000100.00000
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): 0.500002.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.200001.00000
Edible ices, including sherbet and sorbet (03.0): 0.500002.50000
Processed fruit (04.1): 0.400002.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 1.000005.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.200001.00000
Bakery wares (07.0): 2.0000010.00000
Meat and meat products, including poultry and game (08.0): 0.200001.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.200001.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.300001.50000
Foodstuffs intended for particular nutritional uses (13.0): 0.500002.50000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.200001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 1.000005.00000
Ready-to-eat savouries (15.0): 2.0000010.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.400002.00000
 
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):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring-substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 58 (FGE.58) Consideration of phenol derivatives evaluated by JECFA (55th meeting) structurally related to ring substituted phenolic substances evaluated by EFSA in FGE.22 (2006) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 60 (FGE.60): Consideration of eugenol and related hydroxyallylbenzene derivatives evaluated by JECFA (65th meeting) structurally related to ring- substituted phenolic substances evaluated by EFSA in FGE.22 (2006)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring-substituted phenolic substances from chemical groups 21 and 25
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :94378
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
1-(4-hydroxy-3-methoxyphenyl)decan-3-one
Chemidplus:0027113220
 
References:
 1-(4-hydroxy-3-methoxyphenyl)decan-3-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):94378
Pubchem (sid):135049884
 
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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10482
HMDB (The Human Metabolome Database):HMDB30801
FooDB:FDB002743
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
FAO:1-(4-Hydroxy-3-methoxyphenyl)-decan-3-one
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 ginger rhizome
PbMd Search Trop Picture
 ginger root oil CO2 extract
PbMd Search Trop Picture
 ginger root oil CO2 extract australia @ 0.08%
Data GC Search Trop Picture
 grains of paradise
Search Trop Picture
 pepper melegueta pepper
PbMd Search Trop Picture
 pepper sichuan pepper
PbMd Search PMC Picture
 
Synonyms:
 bisabolol, hydroxymethoxyphenyl decanone
3-decanone, 1-(4-hydroxy-3-methoxyphenyl)-
1-(4-hydroxy-3-methoxyphenyl)-3-decanone
1-(4-hydroxy-3-methoxyphenyl)-decan-3-one
1-(4-hydroxy-3-methoxyphenyl)decan-3-one
[6]-paradol
5-paradol
 symdecanox HA (Vigon)
 symrelief S (Symrise)
 

Articles:

Google Patents:AROMA COMPOSITION FOR REDUCING OR SUPPRESSING AN UNDESIRED BITTER
EU Patents:AROMA COMPOSITION FOR REDUCING OR SUPPRESSING AN UNDESIRED BITTER, ASTRINGENT IMPRESSION
PubMed:Neuroprotective effect of 6-paradol in focal cerebral ischemia involves the attenuation of neuroinflammatory responses in activated microglia.
Google Patents:Formulation with irritation reducing action comprising bisabolol and [6]-paradol
PubMed:Anti-inflammatory activity of grains of paradise (Aframomum melegueta Schum) extract.
PubMed:Relationship between the acyl chain length of paradol analogues and their antiobesity activity following oral ingestion.
PubMed:6-Shogaol from dried ginger inhibits growth of prostate cancer cells both in vitro and in vivo through inhibition of STAT3 and NF-κB signaling.
PubMed:Synthesis of analogues of gingerol and shogaol, the active pungent principles from the rhizomes of Zingiber officinale and evaluation of their anti-platelet aggregation effects.
PubMed:[6]-shogaol inhibits growth and induces apoptosis of non-small cell lung cancer cells by directly regulating Akt1/2.
PubMed:Protective effects of [6]-paradol on histological lesions and immunohistochemical gene expression in DMBA induced hamster buccal pouch carcinogenesis.
PubMed:Enzyme-assisted extraction of bioactive compounds from ginger (Zingiber officinale Roscoe).
PubMed:A new phenanthrene derivative and two diarylheptanoids from the roots of Brassica rapa ssp. campestris inhibit the growth of cancer cell lines and LDL-oxidation.
PubMed:Grains of paradise (Aframomum melegueta) extract activates brown adipose tissue and increases whole-body energy expenditure in men.
PubMed:Putative mycobacterial efflux inhibitors from the seeds of Aframomum melegueta.
PubMed:Phenylpropanoid ester from Zingiber officinale and their inhibitory effects on the production of nitric oxide.
PubMed:Chemopreventive and antioxidant efficacy of (6)-paradol in 7,12-dimethylbenz(a)anthracene induced hamster buccal pouch carcinogenesis.
PubMed:Extract of grains of paradise and its active principle 6-paradol trigger thermogenesis of brown adipose tissue in rats.
PubMed:Quantitative analysis of ginger components in commercial products using liquid chromatography with electrochemical array detection.
PubMed:Cyclooxygenase-2 inhibitors in ginger (Zingiber officinale).
PubMed:Compounds from Sichuan and Melegueta peppers activate, covalently and non-covalently, TRPA1 and TRPV1 channels.
PubMed:Modulation of macrophage functions by compounds isolated from Zingiber officinale.
PubMed:In vitro and in vivo modulation of testosterone mediated alterations in apoptosis related proteins by [6]-gingerol.
PubMed:Cancer preventive properties of ginger: a brief review.
PubMed:Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production.
PubMed:Anti-tumor-promoting activities of selected pungent phenolic substances present in ginger.
PubMed:Effective anti-platelet and COX-1 enzyme inhibitors from pungent constituents of ginger.
PubMed:[Studies on the supercritical-CO2 fluid extraction and quality evaluation of ginger oils].
PubMed:Induction of apoptosis and caspase-3 activation by chemopreventive [6]-paradol and structurally related compounds in KB cells.
PubMed:Antioxidative and antitumor promoting effects of [6]-paradol and its homologs.
PubMed:Effect of ginger constituents and synthetic analogues on cyclooxygenase-2 enzyme in intact cells.
PubMed:Inhibition of epidermal growth factor-induced cell transformation and activator protein 1 activation by [6]-gingerol.
PubMed:Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances.
PubMed:Induction of apoptosis in HL-60 cells by pungent vanilloids, [6]-gingerol and [6]-paradol.
PubMed:Antimicrobial effectiveness of six paradols. 1: A structure-activity relationship study.
 
Notes:
induces apoptosis. From grains of paradise (Amomum melegueta) and ginger (Zingiber officinale) Paradol is the active flavor constituent of the seeds of Guinea pepper (Aframomum melegueta). The seed is also known as Grains of paradise. Paradol has been found to have antioxidative and antitumor promoting effects. It is used in flavors as an essential oil to give spiciness. (Wikipedia)
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