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Geranyl Acetone Synthesis Essay

 
(E)-geranyl acetone
(E)-geranylacetone
 
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      Product(s):
      717 GERANYL ACETONE ≥96.5% (sum of isomers), Kosher
      SDS
      Adds a nice tropical fruit note with pear, rose, woody undertones.
      Used in cherry, stone fruits, pear, apple, peach, raspberry, coconut and tomato flavors.
       
       
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      Product(s):
      07-12000 GERANYL ACETONE, Kosher
      07-12055 GERANYL ACETONE NATURAL 5% IN ETHYL ALCOHOL, Kosher
       
    • Sigma-Aldrich
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      Product(s):
      W354201 6,10-Dimethyl-5,9-undecadien-2-one, ≥97%, stabilized, FG
      SDS
       
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      Product(s):
      G0236 Geranylacetone [mixture of (E)- and (Z)- isomers, (3:2)] >96.0%(GC)
       
(5E)-6,10-dimethylundeca-5,9-dien-2-one (Click)
IUPAC Name: (5E)-6,10-dimethylundeca-5,9-dien-2-one
Std.InChI: InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9+
InChI: InChI=1/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9+
Std.InChIKey: HNZUNIKWNYHEJJ-FMIVXFBMSA-N
InChIKey: HNZUNIKWNYHEJJ-FMIVXFBMBN
SMILES: CC(=CCC/C(=C/CCC(=O)C)/C)C
CAS Number: 3796-70-1
ECHA EINECS - REACH Pre-Reg: 223-269-8
FDA UNII: 9B7RY79U9Z
Nikkaji Web: J24.231D
Beilstein Number: 1722277
MDL: MFCD00008910
CoE Number: 11088
XlogP3-AA: 3.70 (est)
Molecular Weight: 194.31754000
Formula: C13 H22 O
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
EFSA/JECFA Comments: JECFA evaluated 6,10-dimethyl-5,9-undecadien-2-one (CASrn as in Register). (R)- or (S)- enantiomer not specified by CASrn in Register. CASrn refers to (E)-isomer. Register name to be changed to (E)-Geranylacetone.
Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Appearance: colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00 % sum of isomers
Food Chemicals Codex Listed: No
Specific Gravity: 0.86100 to 0.86700 @  25.00 °C.
Pounds per Gallon - (est).: 7.164 to  7.214
Refractive Index: 1.46300 to 1.47100 @  20.00 °C.
Boiling Point: 92.00 to  93.00 °C. @ 2.50 mm Hg
Boiling Point: 247.00 °C. @ 760.00 mm Hg
Acid Value: 1.00 max. KOH/g
Vapor Pressure: 0.016000 mm/Hg @ 25.00 °C. (est)
Vapor Density: >1 ( Air = 1 )
Flash Point: 230.00 °F. TCC ( 110.00 °C. )
logP (o/w): 4.129 (est)
Shelf Life: 12.00 month(s) or longer if stored properly.
Storage: store in cool, dry place in tightly sealed containers, protected from heat and light.
Soluble in:
 alcohol
 water, 8.867 mg/L @ 25 °C (est)
Insoluble in:
 water
Odor Type: floral
Odor Strength: medium
 fresh  green  fruity  waxy  rose  woody  magnolia  tropical  
Odor Description:
at 100.00 %. 
fresh green fruity waxy rose woody magnolia tropical
Luebke, William tgsc, (2007)
 green  fruity  waxy  woody  pear  rose  guava  tropical  
Odor Description:
Green, fruity, waxy, woody, pear, rosy and guava with tropical nuances
Mosciano, Gerard P&F 23, No. 1, 33, (1998)
 floral  fruity  green  tropical  pear  banana  ylang  fatty  
Taste Description:
floral fruity green tropical pear banana ylang fatty
 floral  fruity  fatty  green  pear  apple  banana  tropical  
Taste Description:
at 12.00 ppm.  
Floral, fruity, fatty, green, pear, apple and banana with tropical nuances
Mosciano, Gerard P&F 23, No. 1, 33, (1998)
Substantivity: 192 Hour(s)
  
Bedoukian Research
GERANYL ACETONE
≥96.5% (sum of isomers), Kosher
Odor: fresh, rose, magnolia-type
Use: Adds a nice tropical fruit note with pear, rose, woody undertones.
Flavor: green fruity
Used in cherry, stone fruits, pear, apple, peach, raspberry, coconut and tomato flavors.
BOC Sciences
For experimental / research use only.
Geranyl Acetone
Indenta Group
Geranyl Acetone
Penta International
GERANYL ACETONE NATURAL 5% IN ETHYL ALCOHOL, Kosher
Penta International
GERANYL ACETONE, Kosher
Reincke & Fichtner
6,10-Dimethyl-5,9-undecadien-2-one
Santa Cruz Biotechnology
For experimental / research use only.
Geranylacetone ≥96%
Shanghai Vigen Fine Chemical
Geranyl Acetone
Sigma-Aldrich
6,10-Dimethyl-5,9-undecadien-2-one, ≥97%, stabilized, FG
Odor: apple; rose; woody; green; vegetable
Certified Food Grade Products
TCI AMERICA
For experimental / research use only.
Geranylacetone [mixture of (E)- and (Z)- isomers, (3:2)] >96.0%(GC)
The Good Scents Company
(E)-geranyl acetone
Odor: fresh green fruity waxy rose woody magnolia tropical
Preferred SDS: View
European information :
Most important hazard(s):
Xi N - Irritant, Dangerous for the environment.
R 38 - Irritating to skin.
R 51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Skin irritation (Category 2), H315
Serious eye damage/eye irritation (Category 2A), H320
Eye irritation (Category 2A), H319
Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
Chronic aquatic toxicity (Category 2), H411
GHS Label elements, including precautionary statements
 
Pictogram
 
Signal word Warning
Hazard statement(s)
H315 - Causes skin irritation
H320 - Causes eye irritation
H319 - Causes serious eye irritation
H335 - May cause respiratory irritation
H411 - Toxic to aquatic life with long lasting effects
Precautionary statement(s)
P261 - Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 - Wash skin thouroughly after handling.
P271 - Use only outdoors or in a well-ventilated area.
P273 - Avoid release to the environment.
P280 - Wear protective gloves/protective clothing/eye protection/face protection.
P302 + P352 - IF ON SKIN: wash with plenty of soap and water.
P304 + P340 - IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P312 - Call a POISON CENTER or doctor/physician if you feel unwell.
P332 + P313 - IF SKIN irritation occurs: Get medical advice/attention.
P337 + P313 - IF eye irritation persists: Get medical advice/attention.
P362 - Take off contaminated clothing and wash before reuse.
P391 - Collect spillage. Hazardous to the aquatic environment
P403 + P233 - Store in a well-ventilated place. Keep container tightly closed.
P405 - Store locked up.
P501 - Dispose of contents/container in accordance with local/regional/national/international regulations.
Oral/Parenteral Toxicity:
oral-rat LD50  > 5000 mg/kg
Dispose of contents/container in accordance with local/regional/national/international regulations.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Dispose of contents/container in accordance with local/regional/national/international regulations.

Inhalation Toxicity:
Not determined
Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for (E)-geranyl acetone usage levels up to:
  10.0000 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 41.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 2.00 (μg/capita/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: 11
Click here to view publication 11
 average usual ppmaverage maximum ppm
baked goods: -10.00000
beverages(nonalcoholic): -10.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -10.00000
fruit ices: --
gelatins / puddings: -10.00000
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: -10.00000
soups: --
sugar substitutes: --
sweet sauces: --
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 7 (FGE.07): Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5
View page or View pdf
Flavouring Group Evaluation 63 (FGE.63): Consideration of aliphatic secondary alcohols, ketones and related esters evaluated by JECFA (59th meeting) structurally related to saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids evaluated by EFSA in FGE.07 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf
Flavouring Group Evaluation 7, Revision 1 (FGE.07Rev1): Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Scientific opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission
View page or View pdf
Flavouring Group Evaluation 7, Revision 2 (FGE.07Rev2) : Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 63, Revision 1 (FGE.63Rev1): Consideration of aliphatic secondary alcohols, ketones and related esters evaluated by JECFA (59th and 69th meetings) structurally related to saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids evaluated by EFSA in FGE.07Rev4 (2012)
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 63, Revision 2 (FGE.63Rev2): Consideration of aliphatic secondary alcohols, ketones and related esters evaluated by JECFA (59th and 69th meetings) structurally related to saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids evaluated by EFSA in FGE.07Rev4
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 63, Revision 3 (FGE.63Rev3): aliphatic secondary alcohols, ketones and related esters evaluated by JECFA (59th and 69th meetings) structurally related to saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids evaluated by EFSA in FGE.07Rev4
View page or View pdf
EPI System: View
EPA Substance Registry Services (TSCA): 3796-70-1
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 1549778
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 (5E)-6,10-dimethylundeca-5,9-dien-2-one
Chemidplus: 0003796701
RTECS: YQ1190000 for cas# 3796-70-1
Potential Blenders and core components note
   




(E)-6,10-Dimethyl-5,9-undecadien-2-one

Formula: C13H22O 
CAS#: 3796-70-1 
MW: 194.31 

[MS]  [ NMR ]  [ Kovats ]  [Behavioural function]  [Occurrence in plant]  [Chemdraw] 



Reference(s) for synthesis of (E)-6,10-Dimethyl-5,9-undecadien-2-one



Dicker, D.W., and Whitting, M.C. 1958. Synthetical studies on terpenoids. Part I. The synthesis of squalene. J. Chem. Soc. 1994-2000.
 
Shimizu, I., Yamada, T., and Tsuji, J. 1980. Palladium-catalyzed rearrangement of allylic esters of acetoacetic acid to give delta,gamma-unsaturated methyl ketones. Tetrahedron Lett. 21:3199-3202.
 

 
Citation: El-Sayed AM 2018. The Pherobase: Database of Pheromones and Semiochemicals. <http://www.pherobase.com>.
© 2003-2018 The Pherobase - Extensive Database of Pheromones and Semiochemicals. Ashraf M. El-Sayed.
Page created on 5-January-2018

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