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Propylidenephthalide

HCID 28500
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Basic information

CAS
17369-59-4
Standard SMILES
CCC=C1OC(=O)c2ccccc21
InChIKey
NGSZDVVHIGAMOJ-UHFFFAOYSA-N
Molecular formula
C11H10O2
Average molar mass
174.2 g/mol
Monoisotopic mass
174.06807956

Overview

3-propylidene phthalide is a clear yellow liquid. (NTP, 1992)

Names & identifiers

Preferred name
Propylidenephthalide
IUPAC
3-propylidene-2-benzofuran-1-one
English name
FEMA 2952
Molecular formula
C11H10O2
Molecular weight
174.2

Names & synonyms

3-PROPYLIDENEPHTHALIDE17369-59-4Propylidene phthalideDTXSID7025972PropylidenephthalideFEMA No. 2952WHD8YJ226PDTXCID70810032RefChem:930068241-402-81(3H)-Isobenzofuranone, 3-propylidene-Phthalide, 3-propylidene-
Show more names
CELERIAXFEMA 2952PROPLIDENE PTHALIDEPROPYLIDINEPHTHALIDEN-PROPYLIDENEPHTHALIDEphthalide,3-propylidene3-N-PROPYLIDENEPHTHALIDE3-Propylidenephthalimide
MFCD000518133-propylidene-1,3-dihydro-2-benzofuran-1-one3-propylideneisobenzofuran-1-oneButylphthalide Impurity 233-propylidene-2-benzofuran-1-one(3Z)-3-propylidene-1,3-dihydro-2-benzofuran-1-oneSCHEMBL317445SCHEMBL11045364

Database identifiers

CAS
17369-59-4
PubChem CID
28500
DTXSID
DTXSID7025972
EC Number
241-402-8

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
13
Formal charge
0
Complexity
242

Experimental & physicochemical properties

CosmeticsCosmetics ingredient -> Fragrance
FragrancesFragrance Ingredient (3-Propylidenephthalide) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 items

1.135 at 74.7 °F (NTP, 1992) - Denser than water; will sink

1.127-1.132

Flavoring AgentsEU Flavoring substances
Solubility · 3 items

less than 0.1 mg/mL at 64 °F (NTP, 1992)

Insoluble in water; soluble in oils

soluble (in ethanol)

Flash Pointgreater than 200 °F (NTP, 1992)
Boiling Point · 2 items

343 to 347 °F at 15 mmHg (NTP, 1992)

169-171 °C (13 mm Hg)

Refractive Index1.557-1.562

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1646 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 1(3H)-Isobenzofuranone, 3-propylidene-

Hazard Traits - Fragrance Allergen

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

1(3H)-Isobenzofuranone, 3-propylidene-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1(3H)-Isobenzofuranone, 3-propylidene-: Environment tier I assessment
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: This chemical can cause irritation of the skin and eyes. When heated to decomposition it emits acrid smoke and fumes. (NTP, 1992)
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity ProfileA ketone and an ether derivative.
Air and Water ReactionsMay be sensitive to prolonged exposure to air and moisture (NTP, 1992). Insoluble in water.

Chemistry & industry

Uses & manufacturing

IFRA Fragrance Standards · 6 items

3-Propylidenephthalide

3-Propylidenephthalide; 1(3H)-Isobenzofuranone, 3-propylidene-; 3-Propylidene-2-benzofuran-1(3H)-one; Propylidene phthalide

IFRA_STD_076.pdf

51

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Restriction: This material should be used only in the limited quantity as stated in the Standard

Household ProductsCosmetics product ingredient: 3-Propylidene-1(3H)-isobenzofuranone (3-Propylidenephthalide)
Use Classification · 3 items

Fragrance Ingredients

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information1(3H)-Isobenzofuranone, 3-propylidene-: ACTIVE
Restriction Limits in the Finished Product (%) · 6 items

0.072 [Products applied to the lips]

0.022 [Products applied to the axillae]

0.43 [Products applied to the face/body using fingertips]

0,40 [Products related to fine fragrances]

0,10 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0,10 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]

Applications · 3 items

OccurrenceReported found in lovage root

Uses3-Propylidenephthalide is used in Celery Essential Oil and preparation method thereof.

General DescriptionClear yellow liquid.

Preparation methods

Related reactions

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Compound notes

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Physical Description · 2 items

3-propylidene phthalide is a clear yellow liquid. (NTP, 1992)

colourless, slightly viscous liquid; warm, spicy-herbaceous aroma

Physicochemical properties

Melting point
5 °C · 5 °C(lit.)
Boiling point
170 °C12 · 170 °C12 mm Hg(lit.)
Density
1.122 g/mL · 1.122 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.586(lit.)
FEMA
2952 · 2952 | 3-PROPYLIDENEPHTHALIDE
FLAVIS Number
10.005 · 10.005 | 3-Propylidenephthalide
Flash point
230 °F · >230 °F
storage temp.
2 · 2-8°C
Appearance
Light yellow to yellow Liquid
Odor
10 % · at 10.00 % in dipropylene glycol. celery herbal cortex lovage maple fenugreek phenolic brothy vegetable brown
Odor Type
herbal
biological source
synthetic
JECFA Number
1168 · 1168
BRN
4486 · 4486
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
Major Application
flavors and fragrances
Cosmetics Ingredients Functions
PERFUMINGFRAGRANCE
InChI
InChI=1S/C11H10O2/c1-2-5-10-8-6-3-4-7-9(8)11(12)13-10/h3-7H,2H2,1H3
InChIKey
NGSZDVVHIGAMOJ-UHFFFAOYSA-N
SMILES
C1(=O)C2=C(C=CC=C2)C(=CCC)O1
LogP
3.19 · 3.19
CAS DataBase Reference
17369 · 17369-59-4(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
3 · 3-PROPYLIDENEPHTHALIDE
FDA 21 CFR
172.515 · 172.515
EWG's Food Scores
1 · 1-3
FDA UNII
8 YJ226P · WHD8YJ226P
EPA Substance Registry System
3 · 3-Propylidenephthalide (17369-59-4)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H317
Precautionary statements
280 · P280-P301+P312+P330-P302+P352
Hazard Codes
Xn
Risk Statements
22 · 22-43
Safety Statements
23 · 23-24/25-37-24
WGK Germany
3 · 3
RTECS
7235000 · NP7235000
TSCA
TSCA listed
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
4 OralSkin · Acute Tox. 4 OralSkin Sens. 1B
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety & protection

Fire FightingFires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Safety data

wgk
3
tsca
TSCA listed
rtecs
NP7235000
risk_code
22-43
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
23-24/25-37-24
Storage Class
10 - Combustible liquids
Hazard statements
H302-H317
Hazard Classifications
Acute Tox. 4 OralSkin Sens. 1B
Precautionary statements
P280-P301+P312+P330-P302+P352

PreparationBy condensing phthalic anhydride and butyric anhydride at 175°C in the presence of sodium butyrate.