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Allyl propyl disulfide

HCID 16591
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
2179-59-1
Standard SMILES
C=CCSSCCC
InChIKey
FCSSPCOFDUKHPV-UHFFFAOYSA-N
Molecular formula
C6H12S2
Average molar mass
148.3 g/mol
Monoisotopic mass
148.03804273

Overview

Allyl propyl disulfide is a clear pale yellow liquid with a pungent odor. (NTP, 1992)

Names & identifiers

Preferred name
Allyl propyl disulfide
IUPAC
1-(prop-2-enyldisulfanyl)propane
English name
Allyl Propyl Disulfide
Molecular formula
C6H12S2
Molecular weight
148.29

Names & synonyms

ALLYL PROPYL DISULFIDE2179-59-14,5-Dithia-1-octeneDisulfide, 2-propenyl propyl2-Propenyl propyl disulfideAllyl propyl disulphideDisulfide, allyl propylPropyl allyl disulfide3-(propyldisulfanyl)prop-1-eneDTXSID8024448FEMA NO. 40730167D73R1T
Show more names
Onion oilFEMA 4073disulfide,allylpropylAllylpropyl persulfideAllylniMe propyldisulfide
DTXCID604448RefChem:554885218-550-71-Allyl-2-propyldisulfaneAllylPropylDisulfide1-(prop-2-enyldisulfanyl)propanePropyl 2-propenyl disulfideMFCD00040072

Database identifiers

CAS
2179-59-1
PubChem CID
16591
DTXSID
DTXSID8024448
ChEMBL
CHEMBL3187351
ChEBI
CHEBI:173628
UNII
0167D73R1T
EC Number

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
50.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
5
Heavy atoms
8
Formal charge
0
Complexity
52.5

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Sulfur Compounds
OdorPungent, irritating odor
TasteTASTE LIKE THAT OF COOKED ONIONS
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 6 items

0.93 at 59 °F (NIOSH, 2024) - Less dense than water; will float

0.9289 g/cu cm at 15 °C

Relative density (water = 1): 0.9

0.999-1.005

0.93

(59 °F): 0.93

Flavoring AgentsEU Flavoring substances
Color/Form · 2 items

Liquid

Pale-yellow liquid

Solubility · 6 items

less than 1 mg/mL at 68 °F (NTP, 1992)

Soluble in diethyl ether, carbon disulfide, and chloroform

Solubility in water: none

Practically insoluble to insoluble in water

Soluble (in ethanol)

Insoluble

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 · 6 items

Warning

H315 (95.8%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 96 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

Hazard information

Regulatory Information · 3 items

Chemical: Disulfide, 2-propenyl propyl

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

Allyl propyl disulfide: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelCombustible Liquid
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 56 °C explosive vapour/air mixtures may be formed.

Fire Potential · 2 items

Combustible.

Moderate

Health HazardsExcerpt from NIOSH Pocket Guide for Allyl propyl disulfide:
Hazards SummaryOne of the allergens in garlic; [Kanerva, p. 1747] A lachrymator; [HSDB] A dermal sensitizer; [ACGIH]
Reactive GroupSulfides, Organic

Chemistry & industry

Pharmacology

Absorption, Distribution and ExcretionThe substance can be absorbed into the body by inhalation and by ingestion.
Cellular LocationsMembrane

Uses & manufacturing

Uses · 2 items

The main volatile oil in onions, it is used as a food flavoring agent. [ACGIH]

Synthetic flavor; food additive

Methods of Manufacturing · 2 items

Treatment of 1-ethylthio-2-propenylthioethene with NaNH2 in liquid ammonia results in formation of Na-1-propenethiolate, which reacts with s-propyl propanethiosulfonate to give propenyl propyl disulfide in good yield.

The chief volatile constituent of onion oil.

Use Classification · 4 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4 items

Reported uses: in baked goods--5.0 ppm; in condiments, pickles--20.0 ppm; in meat, meat sauces, Soups--12.75 ppm.

SULFUR-CONTAINING COMPD LISTED ON THE FEMA-GRAS LIST--PROPENYL PROPYL DISULFIDE.

FEMA No. 3227.

The chief volatile constituent of onion oil

Applications · 3 items

OccurrenceReported as the chief volatile constituent in onion oil and found in raw cabbage, chive, garlic oil, leek and onion.

UsesThis chemical,Allyl Propyl Disulfide which occurs in natural food products, could find use in flavor reconstitution of soups, meat preserves, etc. in spice blends, sausages, etc. It is conceivable that it would be permissible in flavor compositions for food products, since it occurs in Garlic, Onion and Asafoetida oils.

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
218-550-7
Nikkaji
J34.822H
Flash Point · 4 items

133.3 °F (NTP, 1992)

133 °F

56 °C

133.3 °F

Boiling Point · 4 items

66-68 °C at 16 mm Hg

195.00 to 200.00 °C. @ 760.00 mm Hg

at 2.1kPa: 66-69 °C

66 °C (10 mm Hg)

DecompositionWhen heated to decomposition it emits highly toxic /sulfur oxides/.
Melting Point · 5 items

5 °F (NTP, 1992)

-15 °C

-15 °C

5 °F

5 °F

Physicochemical properties

Melting point
-15 °C · -15°C
Boiling point
69 °C · 69 °C / 16mmHg
Density
0.99 · 0.99
refractive index
1.516 · 1.5160-1.5200
FEMA
4073 · 4073 | ALLYL PROPYL DISULFIDE
FLAVIS Number
12.021 · 12.021 | Allyl propyl disulfide
Flash point
56 °C · 56 °C
storage temp.
2 · Keep in dark place,Inert atmosphere,2-8°C
form
Pale yellow oil
color
Colorless to Light yellow to Light orange
Odor
Powerful onionlike-garlic-like odor.
Odor Type
sulfurous
Water Solubility
0.1 g/100 · Insoluble. <0.1 g/100 mL at 20 ºC
JECFA Number
1700 · 1700
Henry's Law Constant
3.5 · 3.5×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
LogP
3.66 · 3.66
CAS DataBase Reference
2179 · 2179-59-1(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
ALLYL PROPYL DISULFIDE
EWG's Food Scores
1 · 1
FDA UNII
167 D73R1T · 0167D73R1T
NIST Chemistry Reference
2 · 2-propenyl propyl disulfide(2179-59-1)
EPA Substance Registry System
Allyl propyl disulfide (2179-59-1)
Symbol(GHS)
2 · GHS02,GHS07
Signal word
Warning
Hazard statements
226 · H226-H315-H317-H319-H335
Precautionary statements
210 · P210-P233-P240-P241+P242+P243-P261-P264-P271-P272-P280-P302+P352+P333+P313+P363-P304+P340+P312-P305+P351+P338+P337+P313-P370+P378-P403+P233-P405-P501
Hazard Codes
Xi
Risk Statements
36 · 36
Safety Statements
26 · 26
RIDADR
1993 · 1993
OEB
A
OEL
2 ppm · TWA: 2 ppm (12 mg/m3), STEL: 3 ppm (18 mg/m3)
RTECS
350000 · JO0350000
HS Code
2930.9 · 2930.90.9250
HazardClass
3.2 · 3.2
PackingGroup
III
Hazardous Substances Data
2179 · 2179-59-1(Hazardous Substances Data)
UN ClassificationUN Hazard Class: 3; UN Pack Group: III
OSHA StandardsPermissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 2 ppm (12 mg/cu m).
Reactivity Profile · 1 item

ALLYL PROPYL DISULFIDE may react vigorously with strong oxidizing agents. Incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. May liberate hydrogen sulfide upon decomposition or reaction with an acid.

Chemical DangersDecomposes on burning. This produces sulfur oxides. Reacts with oxidants.
Flammable LimitsCombustible Liquid

Safety & protection

Fire Fighting · 2 items

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use foam, dry powder, carbon dioxide.

First Aid Measures · 3 items

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

First Aid · 2 items

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.

(General first aid procedures)

Safe StorageSeparated from oxidants.
Exposure Control and Personal Protection2.0 [ppm]
Fire Fighting ProceduresTo fight fire use foam, carbon dioxide, or dry chemical.
Storage ConditionsSeparated from oxidants.
Cleanup MethodsCollect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Chemical protection suit including self-contained breathing apparatus.
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 60-70% 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.

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 item

Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 5 items

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

/To prevent inhalation exposure use/ ventilation, local exhaust, or breathing protection. /from table/

/To prevent skin exposure use/ protective gloves. /Should exposure occur,/ remove contaminated clothes. Rinse and then wash skin with water and soap. /from table/

/To prevent eye exposure use/ safety goggles, or eye protection in combination with breathing protection. /Should exposure occur,/ first rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. /from table/

Do not eat, drink, or smoke during work. /from table/

Toxicology

Target OrgansEyes, respiratory system
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a structure estimation method(2), indicates that allyl propyl disulfide is expected to have moderate mobility in soil(SRC). Volatilization of allyl propyl disulfide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.7X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Allyl propyl disulfide is expected to slowly volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.39 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a structure estimation method(2), indicates that allyl propyl disulfide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.7X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 hours and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 140(SRC), from an estimated log Kow of 3.70(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), allyl propyl disulfide, which has an estimated vapor pressure of 0.39 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase allyl propyl disulfide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.4 hours(SRC), calculated from its rate constant of 2.7X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Allyl propyl disulfide does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1 item

In a 1995 Japanese study of stir-fried garlic, the volatile extracts contained 0.27% allyl propyl disulfide(1). A similar study of raw garlic in 1989 found that the oil extracts contained 5.53-6.77X10-6 g/g garlic bulb and volatile water extracts contained 0.10-0.27X10-6 g/g garlic bulb(2).

Adverse EffectsLacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation and by ingestion.

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 4 items

Burning sensation. Cough. Chest tightness. Nausea. Vomiting.

Burning sensation. Redness.

Redness. Pain. Watering of the eyes.

irritation eyes, nose, respiratory system; lacrimation (discharge of tears)

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of allyl propyl disulfide can be estimated to be 500(SRC). According to a classification scheme(2), this estimated Koc value suggests that allyl propyl disulfide is expected to have moderate mobility in soil.

Natural Pollution SourcesAllyl propyl disulfide is the chief volatile constituent in onion oil(1).
Atmospheric Concentrations · 1 item

SOURCE DOMINATED: A study of household waste in Denmark evaluated the volatile components collected from the head space of sanitation collection trucks; allyl propyl disulfide was identified as a volatile organic constituent in an unspecified amount(1).

Human Toxicity Excerpts · 3 items

/HUMAN EXPOSURE STUDIES/ Concentrations of allyl propyl disulfide were measured in an onion dehydrating plant ... Irritation to the eyes, nose, and throat occurred at various operations evolving onion oil, but were most pronounced ... where an average concentration of 3.4 ppm was found.

/HUMAN EXPOSURE STUDIES/ Administration of allyl propyl disulfide to six normal volunteers after a 12-hr fast caused a significant fall in the blood glucose levels and a significant rise in the serum insulin levels during the subsequent 4 hr.

/OTHER TOXICITY INFORMATION/ Allyl propyl disulfide ... is said to be one of the principal volatile substances in onion which irritate the eyes and cause lacrimation.

Artificial Pollution SourcesAllyl propyl disulfide's production and use as a synthetic flavor and food additive(1) may result in its release to the environment through various waste streams.
Environmental Bioconcentration · 1 item

An estimated BCF of 140 was calculated for allyl propyl disulfide(SRC), using an estimated log Kow of 3.70 (1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

Safety data

OEB
A
OEL
TWA: 2 ppm (12 mg/m3), STEL: 3 ppm (18 mg/m3)
rtecs
JO0350000
ridadr
1993
hs_code
2930.90.9250
risk_code
36
Signal word
Warning
Symbol(GHS)
GHS02,GHS07
hazard_code
Xi
safety_code
26
hazard_class
3.2
packing_group
III
Hazard statements
H226-H315-H317-H319-H335
Precautionary statements
P210-P233-P240-P241+P242+P243-P261-P264-P271-P272-P280-P302+P352+P333+P313+P363-P304+P340+P312-P305+P351+P338+P337+P313-P370+P378-P403+P233-P405-P501
Hazardous Substances Data
2179-59-1(Hazardous Substances Data)

General DescriptionClear pale yellow liquid with a pungent odor.

Upstream & downstream products

Downstream products

Ethyl methyl disulfide

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
山东鑫赢舜新材料有限公司0531-13220555910 15168808500 · [email protected]
上海颖心实验室设备有限公司021-59178156 17002132182 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
湖北兴琰新材料科技有限公司13129948835 · [email protected]
山东昌元化学有限公司0531-15554118484 15554118484 · [email protected]
石家庄利达化学品有限公司+86 (311) 8573-7996 · [email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
吉良化学21-62165282 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
湖北广奥生物科技有限公司027-02702759223056 18162699093 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
陕西麟邦实业有限公司17709134430 · [email protected]
吉水县益康天然香料油提炼厂0796-8128936 19070600085 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
郑州鸿晟医药科技有限公司0371-0371-13526885213 15637198702 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
南京多隆生物科技有限公司18905173768 · [email protected]
陕西晶和医药科技有限公司029-86062279 13324594253 · [email protected]
武汉弘德悦欣医药科技有限公司027-83855396 15271852016 · [email protected]
盖米科技(青岛)有限公司19524370118 · [email protected]
安徽进博香料有限公司15102127101 15556562013 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
石家庄元冲生物科技有限公司+86-18033710157 18033710157 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
广东翁江化学试剂有限公司0751-2815987 13927875076 · [email protected]
武汉峰耀同辉化学制品有限公司027-87466205 15377579727 · [email protected]
湖北恒绿源科技有限公司027-88188016 18717196322 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
武汉沃轩科技有限公司13322067656 · [email protected]
武汉裕清嘉衡药业有限公司027-83850122 13343472658 · [email protected]

Additional notes

DefinitionChEBI: 2-Propenyl propyl disulfide is an organosulfur compound.