Sorbic acid
- Iupac Name：(2E,4E)-hexa-2,4-dienoic acid
- CAS No.: 110-44-1
- Molecular Weight：112.12700
- Modify Date.: 2022-11-05 03:59
- 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.
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1. Names and Identifiers
- 1.1 Name
- Sorbic acid
- 1.2 Synonyms
(2E,4E)-2,4-Hexadienoic acid (2E,4E)-hexa-2,4-dienoic acid (2E,4E)hexa-2,4-dienoic acid (E,E)-2,4-Hexadienoic acid (E,E)-hexa-2,4-dienoic acid 2,4-Hexadienoic acid 2,4-Hexadienoic acid, (2E,4E)- 2,4-Hexadienoic acid, (E,E)- all-E-sorbic acid C6:2n-2,4 EINECS 203-768-7 FEMA 3921 hexa-2 hexadienoic acid MFCD00002703 Panosorb sorbic sorbinic acid Sorbinsure Sorbistat trans,trans-2,4-hexadienoic acid trans,trans-sorbic acid trans-trans-2,4-Hexadienoic 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
- 2.1 Density
- 1,205 g/cm3
- 2.1 Melting point
- 132-135°C(lit.)
- 2.1 Boiling point
- 228°C
- 2.1 Refractive index
- 1.4600 (estimate)
- 2.1 Flash Point
- 127 °C
- 2.2 Precise Quality
- 112.05200
- 2.2 PSA
- 37.30000
- 2.2 logP
- 1.20330
- 2.2 Solubility
- ethanol: 0.1?g/mL, clear
- 2.3 VaporDensity
- 3.87 (NTP, 1992) (Relative to Air)
- 2.4 Appearance
- White to pale yellow crystalline powder
- 2.5 Storage
- Ambient temperatures.
- 2.6 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.
- 2.7 Chemical Properties
- White, crystalline solid. Slightly soluble in water andmany organic solvents. Combustible.
- 2.8 Color/Form
- Powder
- 2.9 Decomposition
- When heated to decomposition it emits acrid smoke and irritating fumes.
- 2.10 Heat of Combustion
- -3107 kJ/mol
- 2.11 Odor
- Relatively odorless
- 2.12 PH
- 3.3 (1.6g/l, H2O, 20°C)
- 2.13 pKa
- 4.76(at 25℃)
- 2.14 Water Solubility
- 1.6 g/L (20 oC)
- 2.15 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)
- 2.16 Stability
- Stability Material saturated with this acid may ignite spontaneously. Incompatible with strong oxidizing agents. May be light sensitive.
- 2.17 StorageTemp
- 2-8°C
- 2.18 Surface Tension
- 53.5 mN/m at 20 deg c (mean surface tension of an aqueous solution of 1 g/L)
3. Use and Manufacturing
- 3.1 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.
- 3.2 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
- 3.3 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.
- 3.4 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
- 3.5 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
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R36/38
- 4.1 Safety Statements
- S26-S36-S24/25
- 4.1 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.
- 4.2 Octanol/Water Partition Coefficient
- Log Kow = 1.33
- 4.3 Fire Hazard
- Sorbic acid is combustible.
- 4.4 Hazard Declaration
- H315-H319-H335
- 4.4 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.
- 4.5 RIDADR
- NONH for all modes of transport
- 4.5 Fire Fighting Procedures
- WATER
- 4.6 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
- 4.7 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.
- 4.8 Caution Statement
- P261-P305 + P351 + P338
- 4.8 Formulations/Preparations
- GRADES: FCC; TECHNICAL
- 4.9 WGK Germany
- 1
- 4.9 RTECS
- WG2100000
- 4.9 Protective Equipment and Clothing
- APPLICATION OF 150 MG TO SKIN FOR 1 HR IN MAN PRODUCED SEVERE IRRITATION.
- 4.10 Report
-
Reported in EPA TSCA Inventory.
- 4.11 Skin, Eye, and Respiratory Irritations
- APPLICATION OF 150 MG TO SKIN FOR 1 HR IN MAN PRODUCED SEVERE IRRITATION.
- 4.12 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):?
Xi,
C,
F
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
- 4.13 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.
- 4.14 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
7. Synthesis Route
110-44-1Total: 2 Synthesis Route
8. Other Information
- 8.0 Usage
- Sorbic acid is used as a preservative and is found in food, cosmetics, and other household products. It acts as a stabilizers and antioxidants.
9. Computational chemical data
- Molecular Weight: 112.12700g/mol
- Molecular Formula: C6H8O2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- 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
- CACTVS Substructure Key Fingerprint: AAADccBgMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACACAgAACCAAAAgCIACDSCAAAAAAAAAAICAAAAEAIBAAAAQAAEAAAAAAAkYAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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skype
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