4254-14-2

Basic information

• Product Name: (R)-(-)-1,2-Propanediol
• Synonyms: (R)-propane-1,2-diol;(2R)-PROPANE-1,2-DIOL;(R)-(-)-PROPYLENE GLYCEROL;(R)-(-)-PROPYLENE GLYCOL;(R)-(-)-PROPANEDIOL;(R)-(-)-1,2-Propyleneglycol;(R)-(-)-1,2-PROPANEDIOL;(R)-1,2-PROPANEDIOL
• CAS NO: 4254-14-2
• Molecular Formula: C₃H₈O₂
• Molecular Weight: 76.09
• Product Categories: Chiral Compounds;Diols;chiral;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry
• Mol File: 4254-14-2.mol
• Article Data: 84

Chemical Properties

• Melting Point: -57C
• Boiling Point: 186-188 °C765 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: colorless to light yellow liquid
• Density: 1.04 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.204mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Miscible with acetone, chloroform, ethanol (95%), glycerin, and water; soluble at 1 in 6 parts of ether; not miscible with light mineral oil or fixed oils, but will dissolve some essential oils.
• PKA: 14.49±0.20(Predicted)
• Sensitive: Hygroscopic
• Merck: 14,7855
• BRN: 1718872
• CAS DataBase Reference: (R)-(-)-1,2-Propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1,2-Propanediol(4254-14-2)
• EPA Substance Registry System: (R)-(-)-1,2-Propanediol(4254-14-2)

Safety Data

• Hazard Codes: F,Xn
• Statements: 20-65-15-10
• Safety Statements: 24/25-43-7/8
• WGK Germany: 1
• F: 3
• Hazardous Substances Data: 4254-14-2(Hazardous Substances Data)

Usage

Description

(R)-(-)-1,2-Propanediol, also known as propylene glycol, is a colorless to light yellow liquid with a sweet, slightly acrid taste. It is a chiral building block that can be used for a variety of chemical syntheses and possesses unique chemical properties, making it a versatile compound in the field of chemistry.

Uses

Used in Chemical Synthesis:
(R)-(-)-1,2-Propanediol is used as a chiral building block for various chemical syntheses due to its unique structure and properties. It serves as a key component in the production of pharmaceuticals, cosmetics, and other industrial chemicals.
Used in Pharmaceutical Industry:
(R)-(-)-1,2-Propanediol is used as an excipient in the pharmaceutical industry for the formulation of liquid and semi-solid dosage forms. Its properties, such as solubility and stability, make it an ideal candidate for drug delivery systems.
Used in Cosmetics Industry:
In the cosmetics industry, (R)-(-)-1,2-Propanediol is used as a humectant, moisturizer, and solvent in various cosmetic products. Its ability to retain moisture and mix with other ingredients makes it a valuable component in the formulation of creams, lotions, and other personal care products.
Used in Food Industry:
(R)-(-)-1,2-Propanediol is used as a humectant and preservative in the food industry. Its ability to retain moisture and extend shelf life makes it a popular choice for the production of baked goods, confectionery, and other food products.
Used in Industrial Applications:
(R)-(-)-1,2-Propanediol is used as a component in the manufacturing of various industrial products, such as unsaturated polyester resins, polyurethanes, and other polymers. Its versatility and compatibility with other materials make it a valuable asset in the development of new materials and technologies.

Production Methods

Propylene is converted to chlorohydrin by chlorine water and hydrolyzed to 1,2-propylene oxide. With further hydrolysis, 1,2- propylene oxide is converted to propylene glycol.

Pharmaceutical Applications

Propylene glycol has become widely used as a solvent, extractant, and preservative in a variety of parenteral and nonparenteral pharmaceutical formulations. It is a better general solvent than glycerin and dissolves a wide variety of materials, such as corticosteroids, phenols, sulfa drugs, barbiturates, vitamins (A and D), most alkaloids, and many local anesthetics. As an antiseptic it is similar to ethanol, and against molds it is similar to glycerin and only slightly less effective than ethanol. Propylene glycol is commonly used as a plasticizer in aqueous film-coating formulations. Propylene glycol is also used in cosmetics and in the food industry as a carrier for emulsifiers and as a vehicle for flavors in preference to ethanol, since its lack of volatility provides a more uniform flavor.

Safety

Propylene glycol is used in a wide variety of pharmaceutical formulations and is generally regarded as a relatively nontoxic material. It is also used extensively in foods and cosmetics. Probably as a consequence of its metabolism and excretion, propylene glycol is less toxic than other glycols. Propylene glycol is rapidly absorbed from the gastrointestinal tract; there is also evidence that it is absorbed topically when applied to damaged skin. It is extensively metabolized in the liver, mainly to lactic and pyruvic acids, and is also excreted unchanged in the urine. In topical preparations, propylene glycol is regarded as minimally irritant,although it is more irritant than glycerin. There have been some reports of contact dermatitis associated with propylene glycol.Some local irritation is produced upon application to mucous membranes or when it is used under occlusive conditions.Parenteral administration may cause pain or irritation when propylene glycol is used in high concentration. Propylene glycol is estimated to be one-third as intoxicating as ethanol, with administration of large volumes being associated with adverse effects most commonly on the central nervous system, especially in neonates and children.Other adverse reactions reported, though generally isolated, include: ototoxicity;cardiovascular effects; seizures; and hyperosmolarity and lactic acidosis, both of which occur most frequently in patients with renal impairment. Adverse effects are more likely to occur following consumption of large quantities of propylene glycol or on adminstration to neonates, children under 4 years of age, pregnant women, and patients with hepatic or renal failure. Adverse events may also occur in patients treated with disulfiram or metronidazole. On the basis of metabolic and toxicological data, the WHO has set an acceptable daily intake of propylene glycol at up to 25 mg/kg body-weight.Formulations containing 35% propylene glycol can cause hemolysis in humans. In animal studies, there has been no evidence that propylene glycol is teratogenic or mutagenic. Rats can tolerate a repeated oral daily dose of up to 30 mL/kg body-weight in the diet over 6 months, while the dog is unaffected by a repeated oral daily dose of 2 g/kg in the diet for 2 years. (mouse, IP): 9.72 g/kg (mouse, IV): 6.63 g/kg (mouse, oral): 22.0 g/kg (mouse, SC): 17.34 g/kg (rat, IM): 0.01 g/kg (rat, IP): 6.66 g/kg (rat, IV): 6.42 g/kg (rat, oral): 0.02 g/kg (rat, SC): 22.5 g/kg

storage

At cool temperatures, propylene glycol is stable in a well-closed container, but at high temperatures, in the open, it tends to oxidize, giving rise to products such as propionaldehyde, lactic acid, pyruvic acid, and acetic acid. Propylene glycol is chemically stable when mixed with ethanol (95%), glycerin, or water; aqueous solutions may be sterilized by autoclaving.Propylene glycol is hygroscopic and should be stored in a wellclosed container, protected from light, in a cool, dry place.

Incompatibilities

Propylene glycol is incompatible with oxidizing reagents such as potassium permanganate.

Regulatory Status

GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (dental preparations; IM and IV injections; inhalations; ophthalmic, oral, otic, percutaneous, rectal, topical, and vaginal preparations). Included in nonparenteral and parenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

InChI:InChI=1/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1

Upstream product

• 50-00-0 formaldehyd 
• 75-56-9 methyloxirane 
• 78-98-8 2-oxopropanal 
• 141859-89-4 1-Dimethylsilanyloxy-propan-2-one 
• 116-09-6 hydroxy-2-propanone 
• 687-47-8 (-)-ethyl lactate 
• 17392-83-5 (R)-Methyl lactate 
• 20263-26-7 (R)-1-triphenylmethylmethoxy-2-propanol 
• 7699-00-5 (R)-Ethyl lactate 
• 61597-96-4 Isobutyl (R)-lactate 
• 1067232-52-3 (4S,1'R,2'R)-3-[1'(m-chlorobenzoyl)-2'hyroxypropan-1'-yl]-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 87037-69-2 (R)-2-(benzyloxy)propan-1-ol 
• 79-33-4 L-Lactic acid 
• 57-55-6 propylene glycol 

Downstream Products

• 15448-47-2 (R)-propylene oxide 
• 20263-26-7 (R)-1-triphenylmethylmethoxy-2-propanol 
• 262423-81-4 (R)-2-hydroxy-propyl methanesulfonate 
• 16606-55-6 (R)-1,2-propylene carbonate 
• 110-98-5 1,1'-oxydipropan-2-ol 
• 113429-86-0 (R)-1-bromo-2-propanol 
• 103775-61-7 (R)-2-hydroxypropyl 4-methylbenzenesulfonate 
• 1006058-80-5 (4R)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxolane 
• 134236-23-0 (R)-propane-1,2-diol diacetate 
• 1073630-41-7 (2R)-2-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}propan-1-ol 
• 1073630-40-6 (2R)-1-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}propan-2-ol 
• 871580-90-4 (1R)-2-bromo-1-methylethyl benzoate 
• 40299-67-0 C₁₇H₂₀O₆S₂ 
• 3946-09-6 (R)-lactaldehyde 

Relevant articles and documents

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Method for synthesizing chiral 1,2-diol compound

The invention relates to a method for synthesizing a chiral 1,2-diol compound, which comprises the following steps: sequentially adding a cobalt catalyst, a ligand, alpha-hydroxy ketone, an organic solvent and silane into a reaction system at 20-30 DEG C in a nitrogen atmosphere, then stirring the mixture, and carrying out column chromatography separation on the obtained product to obtain the chiral 1,2-diol compound. The high-yield cobalt catalyst in the earth crust is used, meanwhile, cheap silane (PMHS, 500 g/298 yuan) is used as a reducing agent, the asymmetric reduction reaction of alpha-hydroxy ketone can be efficiently achieved under the mild condition, and the chiral 1,2-diol compound with high yield and optical activity is obtained. Moreover, through the creative labor of the inventor, the reaction yield can reach 99%, and meanwhile, the content of the target product in the generated reaction product is 99% (namely, the yield is 99%, 99% ee).

An alternative stereoselective total synthesis of (-)-pyrenophorol

The total synthesis of 16-membered C2–Symmetric dilactone (-)-Pyrenophorol was accomplished starting from commercially available (S)-epoxide prepared by hydrolytic kinetic resolution of (±)–epoxide with key steps of Grignard reaction, Swern oxidation, Wittig reaction and cyclization was achieved by intermolecular Mitsunobu cyclization. The synthesis of (-)-Pyrenophorol accomplished from cheaply available starting material, easily work-up procedures and reduction of cost in industrial process were major advantages of this route.