hexadienoic acid
2,4-Hexadienoic acid
CAS: 110-44-1
Molecular Formula: C6H8O2
hexadienoic acid - Names and Identifiers
hexadienoic acid - Physico-chemical Properties
| Molecular Formula | C6H8O2 |
| Molar Mass | 112.13 |
| Density | 1.2 g/cm3 at 20 °C |
| Melting Point | 132-135 °C (lit.) |
| Boling Point | 228°C |
| Flash Point | 127 °C |
| JECFA Number | 1176 |
| Water Solubility | 1.6 g/L (20 ºC) |
| Solubility | Slightly soluble in water, easily soluble in methanol, ethanol, glacial acetic acid, acetone, soluble in acetone, benzene, carbon tetrachloride. |
| Vapor Presure | 0.01 mm Hg ( 20 °C) |
| Appearance | White crystalline powder |
| Color | White or cream-white |
| Merck | 14,8721 |
| BRN | 1741831 |
| pKa | 4.76(at 25℃) |
| PH | 3.3 (1.6g/l, H2O, 20°C) |
| Storage Condition | 2-8°C |
| Stability | Stability Material saturated with this acid may ignite spontaneously. Incompatible with strong oxidizing agents. May be light sensitive. |
| Sensitive | Sensitive to heat |
| Refractive Index | 1.4600 (estimate) |
| MDL | MFCD00002703 |
| Physical and Chemical Properties | Character white crystalline powder. Odorless and odorless. melting point 134.5 ℃ boiling point 228 ℃ (decomposition) flash point 127 ℃ solubility soluble in ethanol and ether, insoluble in water. |
| Use | Widely used in food, beverage, pickles, tobacco, medicine, cosmetics, agricultural products and other industries |
hexadienoic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R36/38 - Irritating to eyes and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 1 |
| RTECS | WG2100000 |
| FLUKA BRAND F CODES | 8 |
| TSCA | Yes |
| HS Code | 29161930 |
| Toxicity | LD50 orally in rats: 7.36 g/kg (Smyth, Carpenter) |
hexadienoic acid - Upstream Downstream Industry
| Raw Materials | Crotonaldehyde Acetic acid Acetic acid Toluene Sodium hydroxide diketene Hydrochloric acid Acetaldehyde |
| Downstream Products | Potassium sorbate |
hexadienoic acid - Reference
| Reference Show more | 1. Shen Yanfei, Zhu Xianna, Yao Cheng, et al. Valve switching ion chromatography technology simultaneously detects sugars, sweeteners and preservatives in beverages [J]. Food Science, 2018(1):311-316. |
hexadienoic acid - Nature
Open Data Verified Data
colorless needle-like crystal or white crystalline j-tryptase, odorless or slightly irritating. mp133 ~ 135 deg C; bp228 deg C (decomposition). Soluble in ethanol, propylene glycol, acetic acid, ethyl ether, acetone, benzene and carbon tetrachloride. When the solubility in water at 30 ℃ is 0. 25%.100 ℃, it is 3. 8%. It is stable to light and heat, but it is easy to be oxidized and colored in the air for a long time.
Last Update：2025-06-10 22:55:16
hexadienoic acid - Preparation Method
Open Data Verified Data
acetic acid by high temperature cracking to produce ketene, and then condensation with crotonaldehyde polyester, and then after hydrolysis, refined to get the finished product.
Last Update：2022-01-01 10:09:51
hexadienoic acid - Standard
Authoritative Data Verified Data
This product is (E, C)- 2, 4-hexadienoic acid containing not less than 99.0% of Ce hfl02 calculated as anhydrous.
Last Update：2024-01-02 23:10:35
hexadienoic acid - Trait
Authoritative Data Verified Data
- This product is a white to yellowish-white crystalline powder with extra odor.
- This product is soluble in ethanol, soluble in ether, and slightly soluble in water.
melting point
The melting point of this product (General 0612) is 132 ~ 136C.
Last Update：2022-01-01 11:20:22
hexadienoic acid - Application
Open Data Verified Data
sorbic acid and potassium sorbate are the most widely used preservatives in the world, which have high antibacterial properties and inhibit the growth and reproduction of fungi, to inhibit the growth of microorganisms and play an antiseptic role, the mold, yeast and many aerobic bacteria have inhibitory effect, but the aerophoric spore forming bacteria and Lactobacillus acidophilus almost ineffective. Widely used in cheese, yogurt and other cheese products, bread and snack products, beverages, fruit juice, jam, pickles and fish products and other food antiseptic. The amount of concentrated fruit and vegetable juice in plastic barrels should not exceed 2 g/kg; In soy sauce, vinegar, jam, hydrogenated vegetable oil, soft candy, dried fish products, instant bean products, cake fillings, bread, cake, the maximum use of moon cake 1. Og/kg, the maximum use in wine and fruit wine 0.8g/kg; In the collagen casing, low salt pickles, sauce, preserved fruit, juice (taste) type beverage and jelly in the maximum use 0. 5g/kg; In fruits and vegetables and carbonated beverages in the maximum use of 0.2g/kg; In the food industry can be used for meat, fish, eggs, 0.0 75g/kg in poultry products
Last Update：2025-08-19 16:24:40
hexadienoic acid - Differential diagnosis
Authoritative Data Verified Data
- take about 0 .2g of this product, add 2M l of ethanol to dissolve, add a few drops of test solution, the color of bromine will fade.
- take this product, add O .lm o l/L hydrochloric acid solution is dissolved and diluted to make about 2, 5 tons of solution per lm l, according to UV-visible spectrophotometry (General rule 0401> determination, there is an absorption maximum at a wavelength of 264nm.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 25) (General rule 0402).
Last Update：2022-01-01 11:20:23
hexadienoic acid - Exam
Authoritative Data Verified Data
clarity and color of the fermentation solution
take this product L 0g, add ethanol 50mi to dissolve, check according to law (General rule 0901 and General Rule 0 9 0 2 ) , the solution should be clear and colorless.
acid
take this product l .O g, Add 30 ml of water and 50ml of isopropanol to dissolve, use O .lm o l/L sodium hydroxide solution adjusted the p H value to 4 .0, dilute with water to 10 0 M l, shake well, take 10ml, add colorless magenta solution (take basic fuchsin 0. l g, add water 6 0 m l, add 10% anhydrous sodium sulfite solution 1 0 m l, shake, add hydrochloric acid 2 m l Dropwise with stirring, add water to 100ml. Place in the dark for more than 12 hours, add 0.2~0 .3g activated carbon, shake, filter, then obtain. If the solution is turbid, it should be filtered before use; If the test solution shows violet color, add activated carbon to decolorize and shake, and place it for 30 minutes with the control solution (take acetaldehyde l.O g, 100ml flask, plus N-propanol diluted to the scale, shake, take the right amount, with the preparation of normal fermentation dilution of 1 m l containing acetaldehyde O. 1 M g solution, take the solution 1. 5M l» add water 4, 5M l and isopropyl alcohol 4ml, shake, then add colorless magenta solution lm l, shake, do not deeper (0. 15%).
moisture
take this product, according to the determination method of moisture (General rule 083 $First method 1), the water content shall not exceed 0.5%.
burning residue
The l.O g of this product shall be taken for inspection according to law (General rule 0841), and the remaining residue shall not exceed.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
Last Update：2022-01-01 11:20:23
hexadienoic acid - Content determination
Authoritative Data Verified Data
take this product about 0 .2 5G, precision weighing, adding neutral ethanol (the phenolphthalein indicator solution was neutral> 25ml dissolved, adding phenolphthalein indicator solution several drops, with sodium hydroxide titration solution (O .lm o l/L) titration. Each lm l sodium hydroxide titration solution (0. lm o l/L) corresponds to 11, 21mg of C6H80 2.
Last Update：2022-01-01 11:20:24
hexadienoic acid - Category
Authoritative Data Verified Data
pharmaceutical excipients, bacteriostatic agents.
Last Update：2022-01-01 11:20:24
hexadienoic acid - Storage
Authoritative Data Verified Data
shade, seal, and store in a cool place.
Last Update：2022-01-01 11:20:24
hexadienoic acid - Reference Information
| FEMA | 3921 | 2,4-HEXADIENOIC ACID, (E,E)- |
| LogP | 1.32 at 20℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| properties | white crystalline powder, hardly soluble in water, easily soluble in ethanol and other organic solvents. |
| food preservative | sorbic acid, also known as sorbic acid, is an acidic preservative for food allowed in China at present, and it is also the most widely used high-efficiency non-toxic food mildew inhibitor in the world. Structural formula CH3CH = CH-CH = CHCOOH. Molecular formula C6H8O2, relative molecular mass is 112.12. Colorless needle-like crystal or white crystalline powder; stable to light and heat, but easy to oxidize and change color; melting point 134.5 ℃, boiling point 228 ℃ (decomposition); the pH value of saturated aqueous solution is 3.6; slightly soluble in water, easily Soluble in methanol, ethanol, glacial acetic acid, acetone, soluble in acetone, benzene, carbon tetrachloride, sour taste, non-toxic. The chemical properties are active and easy to undergo addition reactions to form saturated compounds. It has antibacterial effect on mold, yeast and aerobic bacteria, and is almost ineffective on anaerobic Clostridium sp (Clostridium spp) and Lactobacillus acidophilus (Lactobacillus acidophilus). sorbic acid and its potassium salt are suitable for use in the range of pH = 4.5~6. Its mechanism of action is to combine with the sulfhydryl group in the microbial enzyme, destroy the action of the enzyme and cause the reproduction to be blocked. Because this product is an unsaturated fatty acid, it can participate in normal metabolism in the body, and finally oxidize to carbon dioxide and water, so it is harmless to the human body. The daily allowable intake (ADI) of human body is 0~25 mg/kg (calculated by sorbic acid), which can be used as preservatives for soy sauce, vinegar, jam, fruit juice, sherbet, wine, pickles, candied fruit, cake, sausage, cheese and canned food (dosage is 0.2~2.0 g/kg). sorbic acid and its sodium salt can inhibit the growth of mold, and can be used as a food preservative for a long time, especially when the pH value is low, it can be used as an undissociated acid to protect the corrosion. Sorbic acid has characteristics that other preservatives do not have, that is, it has a strong anti-corrosion selectivity. It can inhibit the growth of harmful bacteria to humans, and it is harmless to bacteria that are beneficial to humans. For example, it can inhibit the growth of cheese mold but does not Affect the growth of bacteria that help cheese mature. Therefore, sorbic acid is widely used as a preservative for cheese, cakes and other pastries in the food industry. The test determined that the maximum allowable amount of sorbic acid in food is 0.1%. Mainly used for cheese, pickled vegetables, dried fruits, fruit juice, fruit syrup, beverages, preserves, bread, candy and other mildew. It is also used for the preservation of fish and meat. It is also used in cosmetics, medicine, feed, etc. Industry is produced by the condensation and redecomposition of crotonaldehyde and ketene. |
| content analysis | take 0.25g of sample (weighing to 0.0001g), dissolve it in 50ml of neutral anhydrous methanol, add 2-3 drops of phenolphthalein test solution (TS-167), titrate it to pink with 0.1mol/L NaOH standard solution, and keep it unchanged for 30s. Sorbic acid (%)= V? C × 0.1121/m(1-Xw) × 100 Xw -- moisture,%;V-volume of sodium hydroxide standard solution consumed, ml; C -- concentration of sodium hydroxide standard solution, mol/L; M-sample mass, g;0.1121-millimolar mass of sorbic acid, g. |
| toxicity | ADI 0~25 mg/kg (including sorbic acid and its salts, calculated as sorbic acid; FAO/WHO,2001). LD50 7360mg/kg (rat, oral). It is easily decomposed by oxidation in the body and excreted from the body. GRAS(FDA,§ 182.3089,2000). |
| usage limit | GB 2760-2001(g/kg): meat, fish, eggs, poultry products, 0.075; Fresh-keeping fruits and vegetables, carbonated drinks, 0.2; Collagen casing, low-salt pickles, sauces, preserves, fruit juice (flavor) beverages, jelly, milk-containing beverages, fruit juice (fruity) ice, 0.5; wine, fruit wine, 0.6; plastic barreled concentrated fruit and vegetable juice 2.0 for food industry; soy sauce, vinegar, jam, hydrogenated vegetable oil, fudge, dried fish products, instant bean food, cakes, stuffing, bread, cakes, moon cakes, instant jellyfish, lactic acid bacteria drinks, fruit juice (fruity) ice, 1.0. FAO/WHO(1984 mg/kg): margarine 1000; Olive 500 for meals; Jam and jelly 1000; Orange peel jelly 500; Processing cheese 3000 (other general cheese is 1000); Dried apricot 500; Pineapple juice 1000 with preservatives (used alone or in combination with benzoic acid, its salts and sulfites, but sulfites shall not exceed 500 and are only used for manufacturing). Japan: Refer to "Potassium Sorbate". Effective for acidic foods. Generally use potassium salt that is easily soluble in water. Since it is easy to volatilize with water vapor during heating, it should be added as much as possible after heating. The method of use varies from product to product. Fish meat products and meat products can be added when ingredients are made and must be fully mixed. For pickled foods, sea urchins, fish and shellfish and Japanese fermented soybean paste, etc., it should be dissolved in acetic acid, ethanol, propylene glycol, etc. as much as possible before use. For smoked cuttlefish, octopus and dried fish scallops, they can be mixed with seasonings. Or spray its ethanol and propylene glycol solution directly. Do not use copper or iron containers when dissolving. Can be used for disinfection of containers. Not effective for heavily contaminated food. |
| use | sorbic acid is currently the most widely used acid food preservative in the world. Under acidic conditions (pH 5~6 below), it has inhibitory effect on mold, yeast and aerobic bacteria, but it is almost ineffective on aerobic spore forming bacteria and Lactobacillus acidophilus. In the food industry, the amount of concentrated fruit and vegetable juice in plastic barrels shall not exceed 2 g/kg; In soy sauce, vinegar, jam, hydrogenated vegetable oil, soft candy, dried fish products, instant bean products, pastry stuffing, bread, cake, moon cake and instant jellyfish lactic acid bacteria beverage, the maximum usage is 11 0 g/kg; In wine and fruit wine, the maximum usage is 0.6 g/kg; the maximum usage amount is 0.5 g/kg in gum salt protein casings, low-salt pickles, sauces, candied fruits, fruit juice (flavor) beverages and jellies. The maximum usage amount is 0.2 g/kg in fresh-keeping and carbonated beverages of fruits and vegetables. The maximum usage amount can be 0.075 g/kg in meat, fish, eggs and poultry products in the food industry. In addition, there are also applications in cosmetics, medicine and feed. Sorbic acid is currently the most widely used antifungal agent for food in the world, which has the effect of inhibiting the growth and reproduction of microorganisms. Its toxicity is only 1/4 of benzoic acid, and there is a tendency to replace benzoic acid. In the food industry, it is mainly used for mildew prevention of cheese, pickled vegetables, dried fruits, fruit juices, fruit syrups, beverages, candied fruits, bread, candies, etc., and also for the preservation of fish and meat. Sorbic acid is also used as a preservative in the pharmaceutical industry, light industry cosmetics, flue-cured tobacco leaves, and as an insecticide. In addition, it is also used to prepare reagents; it is used as an unsaturated acid in the resin, perfume and rubber industries; it is also used in feed. Used in pesticide preparation and synthetic rubber industry, and also used as food preservation agent New food preservatives can effectively inhibit the growth of bacteria, mold and yeast, and have no adverse effects on food. It can participate in human metabolism. It is an internationally recognized safe food preservative. It can also be used in the pharmaceutical industry, light industry, cosmetics and other industries. As an unsaturated acid, it can also be used in resin, perfume and rubber industries. |
| production method | 1. ketene method This method is currently widely used in industrial production in the world. Acetic acid is cracked at high temperature to produce ketene, and then condensed with crotonaldehyde to synthesize polyester, and then hydrolyzed and refined to obtain the finished product. Raw material consumption quota: ethylene ketone 510kg/t, crotonaldehyde 1100kg/t. 2. The malonic acid method is obtained by condensation and decarboxylation of malonic acid and crotonaldehyde. 3. Acetone method is obtained by condensation of acetone and crotonaldehyde and dehydrogenation. sorbic acid can be produced by sorbic aldehyde oxidation method, acetone and crotonaldehyde condensation method and malonic acid and crotonaldehyde condensation method, but the current domestic and foreign use of ketene production. In addition, the butadiene route has a good development prospect due to the low cost of raw materials. Butadiene route butadiene and acetic acid under the catalysis of manganese acetate, 140 ℃ pressure condensation to obtain γ-ethylene-γ-butyrolactone under 100 ℃, under acidic conditions, γ-ethylene-γ-butyrolactone can be hydrolyzed to obtain sorbic acid. Acetic acid vapor containing alkyl phosphate catalyst stays in a cracking tube above 700°C for 0.3s, and the generated gas mixture is deactivated by converting the catalyst into ammonium phosphate with ammonia gas. Cooling to -10~30 ℃ step by step to remove water, acetic acid and acetic anhydride, etc.; ketene gas is absorbed by crotonaldehyde and is catalyzed by boron fluoride (or zinc chloride, chloride drill, etc.) to form polyhexene -4,5-β-lactone (polyester for short); polyester is hydrolyzed under acidic conditions, and crude sorbic acid is precipitated after cooling, and then recrystallized with 3 to 4 times the amount of 60% ethanol to obtain sorbic acid. sorbic acid can be produced by sorbic aldehyde oxidation method, acetone and crotonaldehyde condensation method and malonic acid and crotonaldehyde condensation method, but the current domestic and foreign use of ketene production. In addition, the butadiene route has a good development prospect due to the low cost of raw materials. (1) Butadiene route. Under the catalysis of manganese acetate, butadiene and acetic acid are condensed under pressure at 140 ℃ to obtain γ-ethylene-γ-butyrolactone. Sorbic acid can be obtained by hydrolysis of γ-ethylene-γ-butyrolactone at 100 ℃ and acidic conditions. (2) ketene method. Acetic acid vapor containing alkyl phosphate catalyst stays for 0.3s in a cracking tube above 700 ℃, and the generated gas mixture is deactivated by converting ammonia sauce catalyst into ammonium phosphate. Cool step by step to -30-10°C to remove water, acetic acid, acetic anhydride, etc. The ketene gas is absorbed by crotonaldehyde and is catalyzed by boron fluoride (or zinc chloride, cobalt chloride, etc.) to form polyhexene-4, 5-β-lactone (polyester for short), polyester Hydrolysis under acidic conditions, precipitate crude sorbic acid after cooling, and then recrystallize with 3-4 times the amount of 60% ethanol to obtain sorbic acid. It is obtained by the reaction of butenal and acetone under the action of a catalyst at about 0°C. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 7360 mg/kg; Oral-mouse LD50: 3200 mg/kg |
| stimulation data | skin-rabbit 1 mg severe |
| flammability hazard characteristics | combustible, spicy and irritating smoke from the fire site |
| storage and transportation characteristics | warehouse low temperature, ventilation, drying |
| fire extinguishing agent | water, carbon dioxide, dry powder, sand |
| spontaneous combustion temperature | >130°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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View History
hexadienoic acid
dibutyl sebacate
Erycette
C.I. Acid Yellow 36 monosodium salt
CLORGYLINE
BETA-AMINO-PROPIONIC ACID
dibutyl sebacate
Erycette
C.I. Acid Yellow 36 monosodium salt
CLORGYLINE
BETA-AMINO-PROPIONIC ACID
Raw Materials for hexadienoic acid
Downstream Products for hexadienoic acid