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3-butylidene phthalide

Chemical Structure

General Material Information

Preferred name 3-butylidene phthalide
Trivial Name Butylidenephthalide
Short Description 3-butylidenephthalide
Formula C12 H12 O2
CAS Number 551-08-6
FEMA Number 3333
Flavis Number 10.024
ECHA Number 208-991-3
FDA UNII S9178G4B3F
MDL MFCD00047319
COE Number 10083
xLogP3-AA 3.20 (est)
NMR Predictor External link
JECFA Food Flavoring 1170 3-butylidenephthalide
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 551-08-6 ; 3-BUTYLIDENEPHTHALIDE
Synonyms
  • 1(3H)-iso benzofuranone, 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
  • 1(3H)-Isobenzofuranone, 3-butylidene-
  • Phthalide, 3-butylidene-
  • 3-Butylidene-1(3H)-isobenzofuranone
  • Butylidenephthalide
  • 3-Butylidenephthalide
  • NSC 325307
  • 3-Butylidene-2-benzofuran-1-one

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

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

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
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

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 188.22604370117
Specific gravity @ 25 °C
Pounds per Gallon
Specific gravity @ 25 °C
Pounds per Gallon 9.136 to 9.178
Boiling Point 319 to 321°C @ 760 mm Hg
Boiling Point 139 to 142°C @ 5 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 3.388 est
Solubility
alcohol Yes
water, slightly Yes
water, 353.5 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Herbal
herbal, lovage, celery, green, vegetable
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 376 hour(s) at 100.00 %
Luebke, William tgsc, (1991) At 10.00 % in dipropylene glycol. herbal lovage celery
Mosciano, Gerard P&F 17, No. 4, 33, (1992) Celery, green, vegetable, lovage-like with a herbal note
Flavor Type: Celery
celery, green, vegetable, herbal
Mosciano, Gerard P&F 17, No. 4, 33, (1992) At 15.00 ppm. Celery, green, vegetable-like with a herbal nuance

Occurrences

Potential Uses

Applications
Odor purposes Celery , Lovage root , Spice
Flavoring purposes Lovage root , Molasses , Tomato , Vegetable
Cosmetic purposes Perfuming agents

Safety Information

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
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
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
Click here to view publication 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
AIDS Citations:Search
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