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

3-butylidene phthalide
3-butylidenephthalide

Sponsors

Flavor Demo Formulas
Name:3-butylidene-2-benzofuran-1-one
CAS Number: 551-08-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-991-3
FDA UNII:S9178G4B3F
MDL:MFCD00047319
CoE Number:10083
XlogP3-AA:3.20 (est)
Molecular Weight:188.22604000
Formula:C12 H12 O2
NMR Predictor:Predict (works with chrome or firefox)
Category:flavor and fragrance 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:1170 3-butylidenephthalide
FLAVIS Number:10.024 (Old)
DG SANTE Food Flavourings:10.024 3-butylidenephthalide
FEMA Number:3333 3-butylidenephthalide
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: 3-BUTYLIDENEPHTHALIDE
 
Physical Properties:
Appearance:yellow clear oily liquid (est)
Assay: 99.00 to 100.00 sum of isomers
Food Chemicals Codex Listed: No
Specific Gravity:1.10300 @ 25.00 °C.
Specific Gravity:1.09800 to 1.10300 @ 25.00 °C.
Pounds per Gallon - est.: 9.136 to 9.178
Boiling Point: 319.00 to 321.00 °C. @ 760.00 mm Hg
Boiling Point: 139.00 to 142.00 °C. @ 5.00 mm Hg
Vapor Pressure:0.001000 mm/Hg @ 25.00 °C. (est)
Flash Point:> 212.00 °F. TCC ( > 100.00 °C. )
logP (o/w): 3.388 (est)
Soluble in:
 alcohol
 water, slightly
 water, 353.5 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: herbal
Odor Strength:medium ,
recommend smelling in a 10.00 % solution or less
Substantivity:376 hour(s) at 100.00 %
herbal lovage celery
Odor Description:at 10.00 % in dipropylene glycol. herbal lovage celery
Luebke, William tgsc, (1991)
Odor sample from: Frutarom Ltd
celery green vegetable lovage herbal
Odor Description:Celery, green, vegetable, lovage-like with a herbal note
Mosciano, Gerard P&F 17, No. 4, 33, (1992)
Flavor Type: celery
celery green vegetable herbal
Taste Description: at 15.00 ppm. Celery, green, vegetable-like with a herbal nuance
Mosciano, Gerard P&F 17, No. 4, 33, (1992)
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
Berjé
Butylidene Phthalate
Happening at Berje
BOC Sciences
For experimental / research use only.
n-Butylidenephthalide
Frutarom
3-BUTYLIDENEPHTHALIDE
Penta International
3-BUTYLIDENE PHTHALIDE, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
n-Butylidenephthalide, (E)+(Z) ≥95%
Sigma-Aldrich
3-Butylidenephthalide, mixture of cis and trans isomers, ≥96%, FG
Certified Food Grade Products
Synerzine
3-Butylidenephthalide
Treatt
3-Butylidene Phthalide
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
 
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.
Human Experience:
2 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 1850 mg/kg
(Moreno, 1980n)

oral-rat LD50 2200 mg/kg
(Posternak, 1965)

oral-rat LD50 1850 mg/kg
Food and Chemical Toxicology. Vol. 21, Pg. 659, 1983.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 21, Pg. 659, 1983.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for 3-butylidene phthalide usage levels up to:
  2.0000 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 8.60 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 7.00 (μg/capita/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: 6
 average usual ppmaverage maximum ppm
baked goods: -8.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: -5.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: -5.00000
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -5.00000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: -5.00000
sugar substitutes: --
sweet sauces: --
 
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):

Flavouring Group Evaluation 27 (FGE.27): One aromatic lactone from chemical group 11[1] - Scientific Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 80 (FGE.80) - Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008)
View page or View pdf

Flavouring Group Evaluation 80, Revision 1 (FGE.80Rev1): Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008)
View page or View pdf

Scientific Opinion on the safety and efficacy of alicyclic and aromatic lactones (chemical group 11) when used as flavourings for all animal species
View page or View pdf

EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):551-08-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :62368
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
3-butylidene-2-benzofuran-1-one
Chemidplus:0000551086
RTECS:TI3692500 for cas# 551-08-6
 
References:
 3-butylidene-2-benzofuran-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:551-08-6
Pubchem (cid):62368
Pubchem (sid):135020319
Pherobase:View
 
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
KEGG (GenomeNet):C16924
HMDB (The Human Metabolome Database):HMDB32061
FooDB:FDB008768
Export Tariff Code:2932.29.6000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
For Odor
alliaceous
dibutyl sulfide
FL/FR
dipropyl disulfide
FL/FR
amber
angelica root oil
FL/FR
camphoreous
dextro-
camphor
FL/FR
verbenone
FL/FR
caramellic
2-iso
butyl-3-methyl pyrazine
FL/FR
fenugreek absolute
FL/FR
fenugreek oleoresin
FL/FR
mesitene lactone
FR
chocolate
2,4,5-
trimethyl thiazole
FL/FR
citrus
methyl heptenone
FL/FR
ocimene quintoxide
FL/FR
coumarinic
phthalide
FL/FR
ethereal
2-
methyl valeraldehyde
FL/FR
floral
hexahydrofarnesyl acetone
FL/FR
hexyl nonanoate
FL/FR
(Z)-
jasmone
FL/FR
iso
jasmone
FL/FR
2-
pentadecanone
FL/FR
(Z)-
rose oxide
FL/FR
fruity
2-
heptyl butyrate
FL/FR
methyl nonanoate
FL/FR
tropical thiazole
FL/FR
green
acetaldehyde butyl phenethyl acetal
FL/FR
iso
butyl benzyl carbinol
FL/FR
iso
butyl methyl ketone
FL/FR
2-iso
butyl pyrazine
FL/FR
2-iso
butyl thiazole
FL/FR
cortex pyridine
FL/FR
cucumber essence
FL/FR
galbanum decatriene
FL/FR
geranium thiazole
FL/FR
(Z)-4-
heptenal
FL/FR
(Z)-2-
hexen-1-ol
FL/FR
(Z)-4-
hexen-1-ol
FL/FR
(Z)-3-
hexen-1-yl (E)-crotonate
FL/FR
(Z)-3-
hexen-1-yl tiglate
FL/FR
4-
hexenol
FL/FR
(Z)-
leaf acetal
FL/FR
methyl heptine carbonate
FL/FR
nerol oxide
FL/FR
(Z,Z)-3,6-
nonadien-1-ol
FL/FR
2-
octen-1-ol
FL/FR
1-
penten-3-ol
FL/FR
iso
propyl decanoate
FL/FR
herbal
apium graveolens seed oil india
FL/FR
3-
butyl phthalide
FL/FR
celery ketone
FL/FR
celery leaf oil
FL/FR
celery seed oil CO2 extract
FL/FR
celery undecene
FR
levisticum officinale herb oil
FL/FR
levisticum officinale root absolute
FL/FR
levisticum officinale root extract
FL/FR
lovage tincture
FL/FR
curled
parsley seed oil
FL/FR
3-
propylidene phthalide
FL/FR
melon
(Z)-6-
nonen-1-ol
FL/FR
minty
carvyl acetate
FL/FR
iso
propyl tiglate
FL/FR
musty
cocoa butenal
FL/FR
roasted
fenugreek resinoid
FL/FR
spicy
iso
butyl angelate
FL/FR
cuminaldehyde
FL/FR
levisticum officinale root oil
FL/FR
sulfurous
grapefruit menthane
FL/FR
3-(
methyl thio) hexanol
FL/FR
tonka
whiskey lactone
FL/FR
vegetable
endo-1,2,3,3-
tetramethyl bicyclo(2.2.1)heptan-2-ol
FR
waxy
methyl octanoate
FL/FR
propyl decanoate
FL/FR
woody
amber dodecane
FR
alpha-
farnesene
FL/FR
alpha-
farnesene isomer
FL/FR
yeasty
2-
octen-4-one
FL/FR
For Flavor
No flavor group found for these
3-
butyl phthalide
FL/FR
2-iso
butyl pyrazine
FL/FR
2-
ethyl-4,5-dimethyl oxazole
FL
2-
heptyl butyrate
FL/FR
(Z)-3-
hexen-1-yl (E)-crotonate
FL/FR
(E)-4-
hexenal
FL
hexyl nonanoate
FL/FR
2-
methyl thiazole
FL
4-(
methyl thio) butanol
FL
2-
methyl-6-propoxypyrazine
FL
iso
propyl decanoate
FL/FR
propyl decanoate
FL/FR
2-iso
propyl pyridine
FL
2-iso
propyl-3-(methyl thio) pyrazine
FL
verbenone
FL/FR
alliaceous
alliaceous
allyl thiopropionate
FL
cyclopentyl mercaptan
FL
dipropyl disulfide
FL/FR
3-
tetrahydrothiophenone
FL
tropical thiazole
FL/FR
amber
iso
butyl benzyl carbinol
FL/FR
brown
fenugreek oleoresin
FL/FR
caramellic
fenugreek absolute
FL/FR
fenugreek resinoid
FL/FR
coumarinic
phthalide
FL/FR
fatty
2-
octen-1-ol
FL/FR
2-
pentadecanone
FL/FR
fruity
2,4-
hexadien-1-ol
FL
green
acetaldehyde butyl phenethyl acetal
FL/FR
angelica root oil
FL/FR
iso
butyl angelate
FL/FR
iso
butyl methyl ketone
FL/FR
2-iso
butyl thiazole
FL/FR
2-iso
butyl-3-methyl pyrazine
FL/FR
celery ketone
FL/FR
cocoa butenal
FL/FR
cortex pyridine
FL/FR
cucumber essence
FL/FR
dibutyl sulfide
FL/FR
dihydroxyacetophenone (mixed isomers)
FL
alpha-
farnesene
FL/FR
alpha-
farnesene isomer
FL/FR
galbanum decatriene
FL/FR
geranium thiazole
FL/FR
(E)-2-
heptenal
FL
(Z)-4-
heptenal
FL/FR
hexahydrofarnesyl acetone
FL/FR
(Z)-2-
hexen-1-ol
FL/FR
(Z)-4-
hexen-1-ol
FL/FR
(Z)-3-
hexen-1-yl tiglate
FL/FR
2-
hexyl pyridine
FL
horseradish oil
FL
iso
jasmone
FL/FR
(Z)-
leaf acetal
FL/FR
methyl heptenone
FL/FR
methyl heptine carbonate
FL/FR
methyl octanoate
FL/FR
4-
methyl thiazole
FL
3-(5-
methyl-2-furyl) butanal
FL
nerol oxide
FL/FR
ocimene quintoxide
FL/FR
2,4-
octadienal
FL
4-
penten-1-yl acetate
FL
1-
penten-3-ol
FL/FR
2-
propyl pyrazine
FL
iso
propyl tiglate
FL/FR
propylene glycol acetone ketal
FL
3-
propylidene phthalide
FL/FR
(Z)-
rose oxide
FL/FR
herbal
apium graveolens seed oil india
FL/FR
celery leaf oil
FL/FR
celery seed oil CO2 extract
FL/FR
celery seed oleoresin
FL
lovage tincture
FL/FR
curled
parsley seed oil
FL/FR
medicinal
dextro-
camphor
FL/FR
metallic
4-
hexenol
FL/FR
3-(
methyl thio) hexanol
FL/FR
minty
carvyl acetate
FL/FR
nutty
2,4,5-
trimethyl thiazole
FL/FR
spicy
cuminaldehyde
FL/FR
levisticum officinale herb oil
FL/FR
levisticum officinale oleoresin
FL
levisticum officinale root absolute
FL/FR
levisticum officinale root extract
FL/FR
levisticum officinale root oil
FL/FR
sulfurous
grapefruit menthane
FL/FR
methyl benzyl disulfide
FL
vegetable
2-
methyl valeraldehyde
FL/FR
2-
octen-4-one
FL/FR
waxy
(Z,Z)-3,6-
nonadien-1-ol
FL/FR
(Z)-6-
nonen-1-ol
FL/FR
winey
methyl nonanoate
FL/FR
woody
(Z)-
jasmone
FL/FR
whiskey lactone
FL/FR
 
Potential Uses:
FRcelery
FL/FRlovage root
FLmolasses
FRspice
FLtomato
FLvegetable
 
Occurrence (nature, food, other):note
 celery leaf
Search Trop Picture
 celery leaf oil
Search Trop Picture
 celery leaf oil @ 0.90%
Data GC Search Trop Picture
 celery root
Search Trop Picture
 celery seed oil
Search Trop Picture
 celery stem oil
Search Trop Picture
 lovage leaf
Search Trop Picture
 lovage root
Search Trop Picture
 
Synonyms:
1(3H)-isobenzofuranone, 3-butylidene-
3-butylidene-1(3H)-isobenzofuranone
3-butylidene-2-benzofuran-1-one
3-butylidene-2-benzofuran-1(3H)-one
3-N-butylidene-phthalide
3-butylidenephthalide
N-butylidenephthalide
 ligusticum lactone
 

Articles:

PubMed:Antinociceptive activity of Ligusticum porteri preparations and compounds.
PubMed:[Study on the constituents of essential oil of Shunaoxin dropping pills by GC-MS].
PubMed:Targeted and untargeted phytochemistry of Ligusticum canbyi: indoleamines, phthalides, antioxidant potential, and use of metabolomics as a hypothesis-generating technique for compound discovery.
PubMed:Effects of natural phytochemicals in Angelica sinensis (Danggui) on Nrf2-mediated gene expression of phase II drug metabolizing enzymes and anti-inflammation.
PubMed:Online isolation and purification of four phthalide compounds from Chuanxiong rhizoma using high-speed counter-current chromatography coupled with semi-preparative liquid chromatography.
PubMed:Antimycobacterials from lovage root (Ligusticum officinale Koch).
PubMed:(Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.
PubMed:Bioactivity-guided fractionation and GC/MS fingerprinting of Angelica sinensis and Angelica archangelica root components for antifungal and mosquito deterrent activity.
PubMed:Identification and comparison of metabolites after oral administration of essential oil of Ligusticum chuanxiong or its major constituent ligustilide in rats.
PubMed:[Study on fingerprint of rhizoma chuanxiong by HPLC-DAD-MS].
PubMed:Simultaneous analysis of seventeen chemical ingredients of Ligusticum chuanxiong by on-line high performance liquid chromatography-diode array detector-mass spectrometry.
PubMed:Separation and identification of the phthalic anhydride derivatives of Liqusticum Chuanxiong Hort by GC-MS, TLC, HPLC-DAD, and HPLC-MS.
PubMed:Anti-competence effects of synthetic phthalide derivatives on platelet-derived growth factor-induced DNA synthesis in primary cultures of rat aorta smooth muscle cells.
PubMed:The structure-activity relationship between synthetic butylidenephthalide derivatives regarding the competence and progression of inhibition in primary cultures proliferation of mouse aorta smooth muscle cells.
 
Notes:
Flavouring ingredient
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