Benzyl alcohol Property
- Melting point:
- -15 °C
- Boiling point:
- 205 °C
- 1.045 g/mL at 25 °C(lit.)
- vapor density
- 3.7 (vs air)
- vapor pressure
- 13.3 mm Hg ( 100 °C)
- refractive index
- 2137 | BENZYL ALCOHOL
- Flash point:
- 201 °F
- storage temp.
- H2O: 33 mg/mL, clear, colorless
- APHA: ≤20
- Mild, pleasant.
- Relative polarity
- explosive limit
- Water Solubility
- 4.29 g/100 mL (20 ºC)
- JECFA Number
- Henry's Law Constant
- <2.70 x 10-7 at 25 °C (thermodynamic method-GC/UV, Altschuh et al., 1999)
- Exposure limits
- No exposure limit is set. Because of its low vapor pressure and low toxicity, the health hazard to humans from occupational exposure should be very low.
- CAS DataBase Reference
- 100-51-6(CAS DataBase Reference)
- NIST Chemistry Reference
- Benzyl alcohol(100-51-6)
- EPA Substance Registry System
- Benzyl alcohol (100-51-6)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 1593 6.1/PG 3
- WGK Germany
- Autoignition Temperature
- 817 °F
- HS Code
- Hazardous Substances Data
- 100-51-6(Hazardous Substances Data)
- LD50 orally in rats: 3.1 g/kg (Smyth)
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- Product number:
- Product name :
- Benzyl alcohol
- analytical standard
- Product number:
- Product name :
- Benzyl alcohol
- analytical standard
- Product number:
- Product name :
- Benzyl Alcohol
- Product number:
- Product name :
- Benzyl alcohol, ACS, 99+%
- Product number:
- Product name :
- Benzyl alcohol, ACS, 99+%
Benzyl alcohol Chemical Properties,Usage,Production
Phenylcarbinol is also known as benzyl alcohol. Its chemical formula is C6H5CH2OH and its density is 1.045 g/mL at 25 ° C (lit). Benzylalcohol is one of the simplest fatty alcohol containing phenyl. It can be seen as benzene substituted by hydroxymethyl, or methyl alcohol substituted by phenyl. It is a colorless transparent sticky liquid with faint aroma. Sometimes benzyl alcohol is placed for a long time, it will smells like bitter almond flavor because of oxidation. Polarity, low toxicity and low steam, so it is used as alcohol solvent. It is combustible, and slightly soluble in water (about 25ml of water soluble 1 gram of benzyl alcohol). It is miscible with ethanol, ethyl ether, benzene, chloroform and other organic solvents.
Benzyl alcohol mainly exists in the form of free or ester in essential oil, such as jasmine oil, ylang-ylang oil, jasmine oil, hyacinth oil, sesame oil, hyacinths balsam, peru balsam and tolu balsam, which all contain this ingredient.
Benzyl alcohol should not be stored for a long time. It can be slowly oxidized to benzaldehyde and anisole in the air.Therefore benzyl alcohol products often smell like almond aroma with characteristic of benzaldehyde. In addition, benzyl alcohol is also easily oxidized to benzoic acid by many kinds of antioxidants such as nitric acid.
Benzyl alcohol has a narcotic effect. It has a strong stimulating effect on the eye, skin and respiratory system. Ingestion, inhalation or skin contact is harmful to the body. One will feel headache, nausea, vomiting, gastrointestinal irritation, convulsion, coma after ingestion of benzyl alcohol. It can lead to death under serious condition. Median lethal dose in rats is 1230mg/kg. When benzyl alcohol enters the body, it is firstly oxidized to benzoic acid and then condenses with glycine in the liver to form hippuric acid and excrets. Intramuscular injection using benzyl alcohol as solvent may result in gluteal muscle contracture.
Function and Use
Benzyl alcohol can be used as preservative of ointments, desiccant of fibers, nylon and plastic film, stabilizer of PVC, photographic developer, solvent of acetate fiber, inks, coatings, paints, epoxy paints, dyes, casein, gelatin, shellac and the like, and intermediate to prepare the benzyl esters or ethers. It also can be used to prepare spices and flavorings (mostly benzyl alcohol ester of fatty acids), which can be used as additive of soaps, perfume, cosmetic and other products. Since the quartz and wool fibers have almostsame refractive index, it can be used to identificate them. In addition, it is used as fixative and diluent inperfume industry.
The hydroxy of benzyl alcohol is very lively. It can react with benzene to generate diphenyl methane, and with acrylonitrile to generate N-benzyl acrylamide (Ritter reaction). It also can react with phosphorus halide and halogen acid to generate benzyl halide. Benzyl halide and benzyl alcohol are benzylation (phenylmethyl) reagent. It can be used as benzyl-protecting group for carboxylic acid and alcohol hydroxy. Benzyl-protecting group can be removed by hydrogenation easily. In addition, benzyl alcohol can also be easily oxidized to benzoic acid by a variety of oxidants. If nitric acid is used, it can be oxidized to aldehyde or acid with different concentration and temperature.
While taking penicillin injections, benzyl alcoholis always used as anesthesia in order to prevent the patient from pain, in which conditions the pain is not too strong. So benzyl alcohol is also known as “painless water”. However, a common clinical side effect is founded: gluteus contracture disease. This is because that benzyl alcohol is not easy to be absorbed by human body. It will chronically accumulate at the injection site, and lead to necrosis of surrounding muscles. In severe cases, it may affect the growth of bone. In 2005, the state food and drug administration issued a ban on benzyl alcohol used as the solvent of penicillin injections.
Transparent colorless liquid. Slightly aromatic odor. Slightly soluble in water, and miscible with alcohol, ether, chloroform and so on.
1.Benzyl alcohol can be used as raw materials and fixatives of spice, pharmaceutical raw materials and anesthetics, preservatives, coloring additives, coatings and solvent of inks. It also can be used to make ballpoint oil.
2.It can be used as chromatographic analysis reagent. And it also can be used in organic synthesis.
3.It can be used for the preparation of sesame oil, drugs and the like. It also can be used as the solvent and fixatives of spice.
4.Benzyl alcoholexists in many fragrant essential oils. Then it can be used as condensing agent with benzyl acetate in jasmine, gardenia, lilac, ylang-ylang, tuberose, hyacinth, acacia and other floral type. It has the fixative effect too. It is often used as the solvent to dissolve artificial musk and other spices. In addition, it can be used as food spices inedible flavor, like cherries, grapes, honey, orange, raspberry, walnut, vanilla.
5.Benzyl alcohol is the edible spice that is temporarily allowed to use. It is mainly used in almonds, oranges, cherries, grapes, strawberries and other fruit-based flavor. The dosage of benzyl alcohol is as the normal production needs. It is usually 1200mg/kg in the chewing gum, 220mg/kg in baked foods, 160mg/kg in cold drinks, 47mg/kg in the candy, and 15mg/kg in soft drinks.
6.Benzyl alcohol is a very useful fixative. It is the indispensable spices to allocate jasmine, polianthes tuberosa, ylang-ylang and other flavorings. It can be used to prepare soaps and daily cosmetics flavorings. But benzyl alcohol can be naturally and slowly oxidized. Part of benzyl alcohol will be oxidized to benzaldehyde and benzyl ether, which makes commercial products with almond scent. It should not be stored for a long time. Benzyl alcohol is widely used in the production of industrial chemicals. It can be used as coating solvent, photographic developer, PVC stabilizer, medicine, solvent of synthetic resin, solvent of vitamin B injection, preservative of unguent or liquid. It also can be used as desiccant of nylon, fiber and plastic film, solvent of dye, cellulose ester and casein, intermediate to prepare benzyl esters or ethers. Meanwhile, it is widely used as pen oil, paint solvent, etc.
7.GB 2760--1996 stipulates that benzyl alcohol can be used as food spices temporarily. It also can be used as fixative agent and grease solvent. As spices, it is mainly used for the preparation of berries, nuts and other flavors.
8.It can be used in organic synthesis. It can be used as solvent of gelatin, casein (heat), cellulose acetate and shellac and the like, microscope embedding material. It also can be used to determinate the contents of vitamin B12.
1.Benzyl chloride with potassium or sodium is heated for a long timg, and hydrolyzes to yield benzyl alcohol.
2.Benzaldehyde in methanol and sodium hydroxide solution react to benzyl alcohol at 65~75 ℃. The product has high purity.
3.Using benzyl chloride as raw materials, it is heated and hydrolyzes to yield benzyl alcohol in the presence of the sodium catalyst. Specification of spices benzyl alcohol(QB792-81): the relative density of 1.041-1.046; refractive index of 1.538-1.541; boiling range 203-206℃ and distillate volume more than 95%; dissolving completely in 30 volumes of distilled water; containing more than 98 percent of alcohol; chlorine test (NF) as the side reaction. Raw material consumption quota: benzyl chloride 1600kg/t; soda ash 1000kg/t.
4.Benzyl alcohol exists naturally in orange flower, ylang-ylang, jasmine, gardenia, acacia, lilac and hyacinth. Benzyl chloride or benzaldehyde is used as raw materials to prepare benzyl alcohol in the industry.
5.Add chlorobenzyl to 12% sodium carbonate solution, heat to 93 ℃ and stir for 5h. Then warm the mixture to 101~103℃ and react for 10h. After the reaction, cool it to the room temperature, and add salt to saturation. After still standing for stratification, take the upper liquid and get crude products through pressure distillation. Then refine to gain the target products. The yield is 70%～72%.
In the presence of sodium hydroxide, formaldehyde and benzaldehyde react to produce benzyl alcohol by disproportionation reaction.
Benzyl alcohol is a component catalyst for epoxy resins. It is also contained in the color developer C-22.
Benzyl alcohol occurs in many
essential oils and foods. It is a colorless liquid with a weak, slightly sweet odor.
Benzyl alcohol can be oxidized to benzaldehyde, for example, with nitric acid.
Dehydrogenation over a copper–magnesium oxide–pumice catalyst also leads to
the aldehyde. Esterification of benzyl alcohol results in a number of important
fragrance and flavor materials. Diphenylmethane is prepared by a Friedel–Crafts
reaction of benzyl alcohol and benzene with aluminum chloride or concentrated
sulfuric acid. By heating benzyl alcohol in the presence of strong acids or strong
bases, dibenzyl ether is formed.
Synthesis. Benzyl alcohol is manufactured mainly by two processes.
1) Benzyl chloride is hydrolyzed by boiling with aqueous solutions of alkali or alkaline-earth hydroxides or carbonates. By-product in this process is dibenzyl ether (up to 10%).
2) Toluene is, in low conversion, oxidized, with air, in the liquid phase, to benzyl hydroperoxide, which yields mainly benzyl alcohol and some benzaldehyde upon hydrolysis, for example, in the presence of a cobalt salt. Benzyl alcohol thus obtained requires a more thorough purification for use in perfumes and flavors.
Because of its relatively weak odor, benzyl alcohol is used in fragrance and flavor compositions mainly as a solvent and for dilution. It is the starting material for a large number of benzyl esters, which are important fragrance and flavor substances.
Benzyl alcohol has a characteristic pleasant, fruity odor and a slightly pungent, sweet taste; the note tends to become similar to that of benzyl aldehyde on aging.
Colorless, hygroscopic, air sensitive liquid with a faint, pleasant, aromatic odor. Odor threshold concentration in water is 10 ppm (Buttery et al., 1988).
The free alcohol is often present in several essential oils and extracts of jasmine, tobacco, tea, neroli, copaiba, Acacia farnesiana Willd., Acacia cavenia Hook. and Arn., Robinia pseudacacia, ylang-ylang, Pandanus odoratissimus, Michelia champaca, Prunus laurocerasus, tuberose, orris, castoreum, violet leaves, clove buds and others. Also found in fresh apple, apricot, mandarin peel oil, high bush blueberry, raspberry, strawberry fruit, American cranberry and cooked asparagus.
Esters of benzyl alcohol are used in makingperfume, soap, flavoring, lotion, and ointment.It finds application in color photography;the pharmaceuticals industry, cosmetics,and leather dyeing; and as an insect repellent.It occurs in natural products such as oils ofjasmine and castoreum.
manufacture of other benzyl Compounds. Pharmaceutic aid (antimicrobial). Solvent for gelatin, casein (when hot), solvent for cellulose acetate, shellac. Used in perfumery and in flavoring (mostly in form of its aliphatic esters). In microscopy as embedding material.
benzyl alcohol is a preservative against bacteria, used in concentrations of 1 to 3 percent. It can cause skin irritation.
Benzyl alcohol is prepared commercially by the distillation of benzyl chloride with potassium or sodium carbonate. It may also be prepared by the Cannizzaro reaction of benzaldehyde and potassium hydroxide.
ChEBI: An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.
An aromatic primary alcohol. Phenylmethanol is synthesized by Cannizzaro’s reaction, which involves the simultaneous oxidation and reduction of benzenecarbaldehyde (benzaldehyde) by refluxing in an aqueous solution of sodium hydroxide:
2C6H5CHO → C6H5CH2OH + C6H5COOH
Phenylmethanol undergoes the reactions characteristic of alcohols, especially those in which the formation of a stable carbonium ion as an intermediate (C6H5CH2 +) enhances the reaction. Substitution onto the benzene ring is also possible; the –CH2OH group directs into the 2- or 4-position by the donation of electrons to the ring.
By the action of alkalis on benzyl chloride
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World Health Organization (WHO)
Benzyl alcohol has been used as an antimicrobial agent in pharmaceutical preparations for many years. Parenteral administration of preparations containing 0.9% benzyl alcohol resulted in the death of 16 neonates in the USA in the early 1980s. Many countries subsequently warned against using such preparations in neonates. This decision is not applicable to the use of benzyl alcohol as a preservative in other circumstances or to its use in topical preparations and no country has placed a total ban on the compound.
Aroma threshold values
Detection: 1.2 to 1000 ppb; also 10 to 1000 ppm.
Taste threshold values
Taste characteristics at 50 ppm: chemical, fruity with balsamic nuances.
A clear colorless liquid with a pleasant odor. Slightly denser than water. Flash point 194°F. Boiling point 401°F. Contact may irritate skin, eyes, and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.
Air & Water Reactions
Slightly soluble in water.
Attacks plastics. [Handling Chemicals Safely 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: an explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73 1967; J, Org. Chem. 28:1893 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].
Inhalation of vapor may cause irritation of upper respiratory tract. Prolonged or excessive inhalation may result in headache, nausea, vomiting, and diarrhea. In severe cases, respiratory stimulation followed by respiratory and muscular paralysis, convulsions, narcosis and death may result. Ingestion may produce severe irritation of the gastrointestinal tract, followed by nausea, vomiting, cramps and diarrhea; tissue ulceration may result. Contact with eyes causes local irritation. Material can be absorbed through skin with anesthetic or irritant effect.
Benzyl alcohol is a low acute toxicant witha mild irritation effect on the skin. Theirritation in 24 hours from the pure compoundwas mild on rabbit skin and moderateon pig skin. A dose of 750 μg producedsevere eye irritation in rabbits. The toxicityof benzyl alcohol is of low order,the effects varying with the species. Oralintake of high concentrations of this compoundproduced behavioral effects in rats.The symptoms progressed from somnolenceand excitement to coma. Intravenous administrationin dogs produced ataxia, dyspnea,diarrhea, and hypermotility in the animals.
Adult and neonatal mice treated withbenzyl alcohol exhibited behavioral change,including sedation, dyspnea, and loss ofmotor function. Pretreatment with pyrazoleincreased the toxicity of benzyl alcohol. Withdisulfiram the toxicity remained unchanged.The study indicated that the acute toxicitywas due to the alcohol itself andnot to bezaldehyde, its primary metabolite(McCloskey et al. 1986).
Benzyl alcohol is combustible.
Reactivity with Water No reaction; Reactivity with Common Materials: Will attack some plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Benzyl alcohol is an antimicrobial preservative used in cosmetics,
foods, and a wide range of pharmaceutical formulations,
including oral and parenteral preparations, at concentrations up
to 2.0% v/v. The typical concentration used is 1% v/v, and it has
been reported to be used in protein, peptide and small molecule
products, although its frequency of use has fallen from 48 products
in 1996, 30 products in 2001, to 15 products in 2006. In
cosmetics, concentrations up to 3.0% v/v may be used as a
preservative. Concentrations of 5% v/v or more are employed as a
solubilizer, while a 10% v/v solution is used as a disinfectant.
Benzyl alcohol 10% v/v solutions also have some local anesthetic properties, which are exploited in some parenterals, cough products, ophthalmic solutions, ointments, and dermatological aerosol sprays.
Although widely used as an antimicrobial preservative, benzyl alcohol has been associated with some fatal adverse reactions when administered to neonates. It is now recommended that parenteral products preserved with benzyl alcohol, or other antimicrobial preservatives, should not be used in newborn infants if at all possible.
Benzyl alcohol is mainly a preservative, mostly used in topical antimycotic or corticosteroid ointments. It is also a component catalyst for epoxy resins and is contained in the color developer C-22. As a fragrance allergen, it has to be mentioned by name in cosmetics within the EU.
Poison by ingestion,intraperitoneal, intravenous, and parenteral routes.Moderately toxic by inhalation, skin contact, andsubcutaneous routes. A moderate skin and severe eyeirritant. Mutation data reported. Combustible liquid.Mixtures with sulfuric ac
Benzyl alcohol is used in a wide variety of pharmaceutical
formulations. It is metabolized to benzoic acid, which is further
metabolized in the liver by conjugation with glycine to form
hippuric acid, which is excreted in the urine.
Ingestion or inhalation of benzyl alcohol may cause headache, vertigo, nausea, vomiting, and diarrhea. Overexposure may result in CNS depression and respiratory failure. However, the concentrations of benzyl alcohol normally employed as a preservative are not associated with such adverse effects.
Reports of adverse reactions to benzyl alcohol used as an excipient include toxicity following intravenous administration; neurotoxicity in patients administered benzyl alcohol in intrathecal preparations; hypersensitivity, although relatively rare; and a fatal toxic syndrome in premature infants.
The fatal toxic syndrome in low-birth-weight neonates, which includes symptoms of metabolic acidosis and respiratory depression, was attributed to the use of benzyl alcohol as a preservative in solutions used to flush umbilical catheters. As a result of this, the FDA has recommended that benzyl alcohol should not be used in such flushing solutions and has advised against the use of medicines containing preservatives in the newborn.
The WHO has set the estimated acceptable daily intake of the benzyl/benzoic moiety at up to 5 mg/kg body-weight daily.
LD50 (mouse, IV): 0.32 g/kg
LD50 (mouse, oral): 1.36 g/kg
LD50 (rat, IP): 0.4 g/kg
LD50 (rat, IV): 0.05 g/kg
LD50 (rat, oral): 1.23 g/kg
By saponification of the ester present in Tolu and Pery balsams; synthetically, it is obtained from benzyl chloride by the action of sodium or potassium carbonate.
In an NTP study, F344 rats were dosed by oral gavage with 0, 200, and 400 mg/kg, 5 days/ week for 2 years. Benzyl alcohol had no effect on the survival of male rats; female rats had reduced survival, and many of the early deaths were considered related to the gavage procedure. There were no treatment-related effects on nonneoplastic or neoplastic lesions in either sex treated with benzyl alcohol. It was concluded that under the conditions of the study, there was no evidence of carcinogenic activity . In the same NTP study, B6C3F1 mice were dosed by oral gavage with 0, 100, and 200 mg/kg, 5 days/week for 2 years. No effects on survival or body weight gain were observed. There were no treatment-related effects on nonneoplastic or neoplastic lesions in either sex. It was concluded that under the conditions of the study, there was no evidence of carcinogenic activity.
Benzyl alcohol naturally occurs in tea (900 ppm), daffodils (165–330 ppm), hyacinths (64–920 ppm), jasmine (120–228 ppm) rosemary (7–32 ppm), hyssop (0.1–30 ppm), tangerines (1–2 ppm), blueberries (0.01–0.08 ppm in fruit juice), ylang-ylang, colocynth, licorice, roselle, tomatoes, spearmint, sweet basil, apricots, tuberose (Duke, 1992), and small-flowered oregano shoots (2 ppm) (Baser et al., 1991). Also identified among 139 volatile compounds identified in cantaloupe (Cucumis melo var. reticulates cv. Sol Real) using an automated rapid headspace solid phase microextraction method (Beaulieu and Grimm, 2001).
Biological. Heukelekian and Rand (1955) reported a 5-d BOD value of 1.55 g/g which is 61.5%
of the ThOD value of 2.52 g/g.
Chemical/Physical. Slowly oxidizes in air to benzaldehyde (Huntress and Mulliken, 1941). Benzyl alcohol will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1993).
Esters of benzyl alcohol are rapidly hydrolysed in vivo to benzyl alcohol, which is then oxidized . The animal organism readily oxidizes benzyl alcohol to benzoic acid, which after conjugation with glycine is rapidly eliminated as hippuric acid in the urine
Benzyl alcohol oxidizes slowly in air to benzaldehyde and benzoic
acid; it does not react with water. Aqueous solutions may be
sterilized by filtration or autoclaving; some solutions may generate
benzaldehyde during autoclaving.
Benzyl alcohol may be stored in metal or glass containers. Plastic containers should not be used; exceptions to this include polypropylene containers or vessels coated with inert fluorinated polymers such as Teflon.
Benzyl alcohol should be stored in an airtight container, protected from light, in a cool, dry place.
It is usually purified by careful fractional distillation under reduced pressure in the absence of air. Benzaldehyde, if present, can be detected by UV absorption at 283nm. It has also been purified by shaking with aqueous KOH and extracting with peroxide-free diethyl ether. After washing with water, the extract is treated with saturated NaHS solution, filtered, washed, dried with CaO and distilled under reduced pressure [Mathews J Am Chem Soc 48 562 1926]. Peroxy compounds can be removed by shaking with a solution of Fe2+ followed by washing the alcohol layer with distilled water and fractionally distilling it. [Beilstein 6 IV 2222.]
Benzyl alcohol is incompatible with oxidizing agents and strong
acids. It can also accelerate the autoxidation of fats.
Although antimicrobial activity is reduced in the presence of
nonionic surfactants, such as polysorbate 80, the reduction is less
than is the case with hydroxybenzoate esters or quaternary
Benzyl alcohol is incompatible with methylcellulose and is only slowly sorbed by closures composed of natural rubber, neoprene, and butyl rubber closures, the resistance of which can be enhanced by coating with fluorinated polymers. However, a 2% v/v aqueous solution in a polyethylene container, stored at 208℃, may lose up to 15% of its benzyl alcohol content in 13 weeks. Losses to polyvinyl chloride and polypropylene containers under similar conditions are usually negligible. Benzyl alcohol can damage polystyrene syringes by extracting some soluble components
Included in the FDA Inactive Ingredients Database (dental injections, oral capsules, solutions and tablets, topical, and vaginal preparations). Included in parenteral and nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Benzyl alcohol Preparation Products And Raw materials Raw materials
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