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Sorbic acid structure
Sorbic acid structure

Sorbic acid

Iupac Name:(2E,4E)-hexa-2,4-dienoic acid
CAS No.:110-44-1
Molecular Weight:112.12700
Introduction:

Mold and yeast inhibitor, fungistatic agent for foods, especially cheeses. To improve characteristics of drying oils. In alkylated type coatings to improve gloss. To improve milling characteristics of cold rubber.

1. Names and Identifiers
1.1 Name
Sorbic acid
1.2 Synonyms

(e,e)-4-hexadienoicacid (E,E)-Sorbic acid 1,3-Pentadiene-1-carboxylic acid 2,4-Hexadienoic Acid 2,4-Hexadienoicacid,(E,E)- 2,4-HEXANEDIENOIC ACID 2e,4e-hexadienoicacid 2-PROPENYL ACRYLIC ACID 4-Hexadienoicacid,(E,E)-2 Hexa-2,4-dienoic acid Sorbic acid

1.3 CAS No.
110-44-1
1.4 CID
643460
1.5 EINECS(EC#)
203-768-7
1.6 Molecular Formula
C6H8O2 (isomer)
1.7 Inchi
InChI=1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+
1.8 InChkey
WSWCOQWTEOXDQX-MQQKCMAXSA-N
1.9 Canonical Smiles
CC=CC=CC(=O)O
1.10 Isomers Smiles
C/C=C/C=C/C(=O)O
2. Properties
3.1 Density
1,205 g/cm3
3.2 Melting Point
132-135°C(lit.)
3.3 Boiling Point
228°C
3.4 Vapour
0.02mmHg at 25°C
3.5 Refractive Index
1.4600 (estimate)
3.6 Flash Point
127 °C
3.7 Appearance
White to pale yellow crystalline powder
3.8 Carcinogenicity
Wistar rats (six males) given subcutaneousinjections of 2mg sorbic acid, in 0.5mL of arachisoil twice weekly for 65 weeks developed local sarcomas. The first tumor was observed at 82 weeks.Similar findings were also observed in follow-up studies. However, six Wistar rats maintained ondrinking water containing 10 mg of sorbic acid/100mLdrinking water for 64 weeks did not develop tumors.Tumors also were not observed inWistar rats (50 of each sex)on diets that contained 40 mg/kg/day of sorbic acid for 18months or in 25 male and female cross-bred white miceafter administration of 40 mg/kg/day for 17 months.Mice fed a diet containing 15% sorbic acid for 88 weeksexhibited a high incidence of hepatoma. Furthermore,the glutathione level in the livers of the mice that ingested15% sorbic acid decreased to 40% of the amount found incontrols after a 3-month feeding period; this low level wasmaintained until the end of the experiments at 12 months.There was a close correlation between the extent of depletionof the glutathione level in the liver and the concentrationof sorbic acid added to the diet. In the same strain of mice feda diet containing 15% sorbic acid for up to 6 months, theacidic fraction of an ether extract showed slight mutagenicactivity in an Ames test with Salmonella typhimurium TA98in the presence of a liver 9000-g supernatant.Consequently, the hepatomas that developed in mice fed a15% sorbic acid diet were considered to be induced both bythe chronic depletion of the hepatic glutathione and by thegradual production of various promutagens in the intestine,which were absorbed and metabolically activated by theliver.
3.9 Chemical Properties
White, crystalline solid. Slightly soluble in water andmany organic solvents. Combustible.
3.10 Color/Form
Powder
3.11 Decomposition
When heated to decomposition it emits acrid smoke and irritating fumes.
3.12 Heat of Combustion
-3107 kJ/mol
3.13 Odor
Relatively odorless
3.14 PH
3.3 (1.6g/l, H2O, 20°C)
3.15 pKa
4.76(at 25℃)
3.16 Solubility
ethanol: 0.1?g/mL, clear
3.17 Spectral Properties
SADTLER REFERENCE NUMBER: 3674 (IR, PRISM); 8305 (IR, GRATING)
MAX ABSORPTION (CHLOROFORM): 260 NM (E= 2400)
IR: 6494 (Coblentz Society Spectral Collection)
UV: 2-70 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 462 (Varian Associates NMR Spectra Catalogue)
MASS: 2-78 (Archives of Mass Spectral Data, John Wiley & Sons, New York)
3.18 Stability
Stability Material saturated with this acid may ignite spontaneously. Incompatible with strong oxidizing agents. May be light sensitive.
3.19 StorageTemp
2-8°C
3.20 Surface Tension
53.5 mN/m at 20 deg c (mean surface tension of an aqueous solution of 1 g/L)
3.21 VaporDensity
3.87 (NTP, 1992) (Relative to Air)
3.22 Water Solubility
Soluble in chloroform, dichlormethane (5 mg/ml-clear, colorless solution),
3. Use and Manufacturing
4.1 Definition
ChEBI: A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometri isomers possible, as well as the one with the highest antimicrobial activity.
4.2 Fire Hazard
Sorbic acid is combustible.
4.3 GHS Classification
Signal: Warning
GHS Hazard Statements
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

Precautionary Statement Codes
P201, P202, P281, P308+P313, P405, and P501
4.4 History
Sorbic acid is a white crystalline solid first isolated in 1859 by hydrolysis of the oil distilled from unripened mountain-ash berries. The name is derived from the scientific term for the rowan tree, Sorbus aucuparia Linne, which is the parent plant of the mountain ash. Sorbic acid was first synthesized in 1900. Interest in this compound was minimal until independent researchers, E. Mueller of Germany and C.M. Gooding of the United States, discovered its antimicrobial effect in 1939 and 1940, respectively. Early interest in manufacturing sorbic acid centered around its use as a tung oil replacement when tung oil supplies were curtailed in the United States during World War II. High manufacturing costs prohibited expanded use until its approval as a food preservative in 1953. Sorbic acid is widely used in foods having a pH of 6.5 or below, where control of bacteria, molds, and yeasts is essential for obtaining safe and economical storage life.
4.5 Purification Methods
Crystallise the acid from water. Dry it air or in a desiccator over P2O5. [Beilstein 2 IV 1701.] Sorbic acid Preparation Products And Raw materials Raw materials
4.6 Safety Profile
Moderately toxic by intraperitoneal and subcutaneous routes. Mildly toxic by ingestion. Experimental reproductive effects. A severe human and experimental skin irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use water. When heated to decomposition it emits acrid smoke and irritating fumes.
4.7 Storage
Ambient temperatures.
4.8 Usage

Mold and yeast inhibitor, fungistatic agent for foods, especially cheeses. To improve characteristics of drying oils. In alkylated type coatings to improve gloss. To improve milling characteristics of cold rubber.

4. Safety and Handling
5.1 Hazard Codes
Xi
5.2 Risk Statements
R36/38
5.3 Safety Statements
S26-S36-S24/25
5.4 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
5.5 Exposure Standards and Regulations
Sorbic acid used as a chemical preservative in food for human consumption is generally recognized as safe when used in accordance with good manufacturing practice.
5.6 Fire Fighting Procedures
WATER
5.7 FirePotential
PAPER, CLOTH & OTHER ABSORBENT MATERIALS SOAKED WITH SORBATES MAY IGNITE SPONTANEOUSLY SO THAT THESE SUBSTANCES SHOULD BE KEPT AWAY FROM CELLULOSIC MATERIALS. /SORBATES/
COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS
5.8 Formulations/Preparations
GRADES: FCC; TECHNICAL
5.9 Octanol/Water Partition Coefficient
Log Kow = 1.33
5.10 Protective Equipment and Clothing
APPLICATION OF 150 MG TO SKIN FOR 1 HR IN MAN PRODUCED SEVERE IRRITATION.
5.11 Report

Reported in EPA TSCA Inventory.

5.12 Safety

Hazard Codes of?Oxireno(9,10)cyclodeca(1,2-b)furan-9(1aH)-one, 2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-,(1aR,4E,7aS,10aS,10bS)- (CAS NO.20554-84-1):?IrritantXi,CorrosiveC,FlammableF
Risk Statements: 11-34?
R11: Highly flammable.?
R34: Causes burns.
Safety Statements: 22-24/25-45-36/37/39-26-16?
S22: Do not breathe dust.?
S24/25: Avoid contact with skin and eyes.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.?
S16: Keep away from sources of ignition.
WGK Germany: 3
RTECS: LY4220000

5.13 Skin, Eye, and Respiratory Irritations
APPLICATION OF 150 MG TO SKIN FOR 1 HR IN MAN PRODUCED SEVERE IRRITATION.
5.14 Specification

??Sorbic acid ,?its cas register number is 110-44-1. It also can be called?(E,E)-2,4-Hexadienoic acid ; 1,3-Pentadiene-1-carboxylic acid, (E,E)- ; 2,4-Hexadienoic acid, (E,E)- ; 2-Propenylacrylic acid ; 2E,4E-Hexadienoic acid ; Acetic acid, (2-butenylidene)- ; Acetic acid, crotylidene- ; EPA Pesticide Chemical Code 075901 ; Hexadienoic acid ; Kyselina 1,3-pentadien-1-karboxylova?; Kyselina sorbova ; Panosorb ; Sorbistat ; alpha-trans-gamma-trans-Sorbic acid ; trans,trans-Sorbic acid ; trans-trans-2,4-Hexadienoic acid .?Sorbic acid (CAS NO.110-44-1) is a white powder or crystals.

5.15 Toxicity
1. ???

skn-man 150?mg/1H SEV

??? JPPMAB ?? Journal of Pharmacy and Pharmacology. 10 (1958),719.
2. ???

skn-rbt 1?mg SEV

??? UCDS** ?? Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 7/14 ,1965.
3. ???

cyt-ham:lng 1050?mg/L

??? FCTOD7 ?? Food and Chemical Toxicology. 22 (1984),501.
4. ???

sce-ham:lng 1050?mg/L

??? FCTOD7 ?? Food and Chemical Toxicology. 22 (1984),501.
5. ???

scu-rat TDLo:1040?mg/kg/65W-I:ETA

??? BJCAAI ?? British Journal of Cancer. 20 (1966),134.
6. ???

orl-rat LD50:7360?mg/kg

??? JIHTAB ?? Journal of Industrial Hygiene and Toxicology. 30 (1948),63.
7. ???

orl-mus LD50:3200?mg/kg

??? 38MKAJ ?? Pattys Industrial Hygiene and Toxicology. 2C (1982),4953.
8. ???

ipr-mus LD50:2820?mg/kg

??? JPPMAB ?? Journal of Pharmacy and Pharmacology. 21 (1969),85.
9. ???

scu-mus LD50:2820?mg/kg

??? JPPMAB ?? Journal of Pharmacy and Pharmacology. 21 (1969),85.
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

Storage

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Computational chemical data
  • Molecular Weight:112.12700g/mol
  • Molecular Formula:C6H8O2
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:112.052429494
  • Monoisotopic Mass:112.052429494
  • Complexity:123
  • Rotatable Bond Count:2
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:2
  • Topological Polar Surface Area:37.3
  • Heavy Atom Count:8
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:2
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
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