ビス(メトキシぎ酸)無水物

オキシビス(ぎ酸メチル) · ピロ炭酸ジメチル · 二炭酸ジメチル · ビス(メトキシぎ酸)無水物 · 2-オキサマロン酸ジメチル · velcorin · DimethylDicarbonate(Dmdc) · Dimethyldicarbonat

https://huagongshe.com/ja/chemical/3086

識別子と物理属性

CAS No.	4525-33-1
分子式	C4H6O5
平均分子量	134.09 g/mol
単同位体質量	134.02152329 g/mol
SMILES	COC(=O)OC(=O)OC
InChIKey	GZDFHIJNHHMENY-UHFFFAOYSA-N
PubChem CID	3086
ChEBI	CHEBI:173546
EC No.	224-859-8
DTXSID	DTXSID2052108
現地名	ビス(メトキシぎ酸)無水物

化学・物理的性質

XLogP	0.7
極性表面積	61.8
水素結合供与体数	0
水素結合受容体数	5
回転可能結合数	4
重原子数	9
形式電荷	0
複雑度	104
食品添加物	ANTIMICROBIAL AGENT -> FDA Substance added to food
密度	1.25 mg/L at 25 °C1.25 g/mL at 25 °C(lit.)
Color/Form	Clear, colorless liquid
溶解度	Soluble in water with decompositionmiscible with toluenedec.35g/l（分解）35g/L (decomposition)
沸点	BP: 44-47 °C at 5 mm Hg45.00 to 46.00 °C. @ 5.00 mm Hg45-46 °C5 mm Hg(lit.)
Decomposition	Hazardous decomposition products: By Fire and Thermal Decomposition: MethanolCarbon oxides, nitrogen oxides (NOx), other potentially toxic fumes.When heated to decomposition it emits acrid smoke and irritating fumes.
融点	15 - 17 °C15-17°C
Food Contact Substances	FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
屈折率	Index of refraction: 1.392 at 20 °C/Dn20/D 1.392(lit.)
Physical Description	Colourless liquid, decomposes in aqueous solution. It is corrosive to skin and eyes and toxic by inhalation and ingestion
自然発火温度	Approximately 465 °C (869 °F)
蒸気圧	0.7 hPa (20 °C)
引火点	80 °C
貯蔵条件	Store below +30°C.
外観・状態	Oil
色	Colourless
爆発限界	3-29.9%(V)
BRN	956715
ヘンリー定数	2.2×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
安定性	Moisture Sensitive
InChI	1S/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3
InChIKey	GZDFHIJNHHMENY-UHFFFAOYSA-N
SMILES	O(C)C(=O)OC(=O)OC
LogP（分配係数）	0.082 (est)
EPAの化学物質情報	Dicarbonic acid, dimethyl ester (4525-33-1)

化学的特性

Dimethyl dicarbonate (DMDC) is a colourless liquid with a slightly pungent aroma. It is primarily used as a beverage preservative, processing aid, or sterilant (Enumber 242). The application of DMDC is particularly useful when wine needs to be sterilized but cannot be sterile filtered, pasteurized, or sulfured. DMDC is also used to stabilize non-alcoholic beverages such as carbonated or non-carbonated juice beverages, isotonic sports beverages, iced teas, and flavored waters.

安全性と法規制

GHS 分類	DangerH226 (23.6%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 106 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報	Chemical: Dicarbonic acid, dimethyl esterRegulation (EC) No 1333/2008 (amended)Dicarbonic acid, dimethyl ester: Does not have an individual approval but may be used under an appropriate group standard
火災の可能性	Combustible
FDA 要件	Dimethyl dicarbonate (CAS Reg. No. 4525-33-1) may be safely used in food in accordance with the following prescribed conditions: (a) The additive meets the following specifications: (1) The additive has a purity of not less than 99.8 percent ... (2) The additive contains not more than 2,000 ppm (0.2 percent) dimethyl carbonate. ... (b) The additive is used or intended for use as a microbial control agent in the following beverages under normal circumstances of bottling, canning, or other forms of final packaging, where the viable microbial load has been reduced to 500 microorganisms per milliliter or less by current good manufacturing practices such as heat treatment, filtration, or other technologies prior to the use of dimethyl dicarbonate: (1) In wine, dealcoholized wine, and low alcohol wine in an amount not to exceed 200 parts per million. (2) In ready-to-drink teas in an amount not to exceed 250 parts per million. (3) In carbonated or noncarbonated, nonjuice-containing (less than or equal to 1 percent juice), flavored or unflavored beverages containing added electrolytes (5-20 milliequivalents/liter sodium ion (Na+) and 3-7 milliequivalents/liter potassium ion (K+)) in an amount not to exceed 250 parts per million. (4) In carbonated, dilute beverages containing juice, fruit flavor, or both, with juice content not to exceed 50 percent, in an amount not to exceed 250 parts per million.
Toxic Combustion Products	Toxic and irritating gases/fumes may be given off during burning or thermal decomposition.
Hazard Classes and Categories	Flam. Liq. 3 (23.6%)

用途

使用

Dimethyl Dicarbonate(DMDC) is a microbial control agent used in wine; ready-to-drink teas; nonjuice-containing beverages; carbonated,dilute beverages containing juice, fruit flavor or both with the juice content not exceeding 50%.Dimethyl Dicarbonate has been commonly used as a antimicrobial agent for a broad spectrum of microorganisms. The primary target microorganisms of DMDC are yeasts, including Saccharomyces, Zygosaccharomyces, Rhodotorula, Candida, Pichia, Torulopsis, Torula, Endomyces, Kloeckera and Hansenula. DMDC is also bactericidal to a number of species including Acetobacter pasteurianus, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, several Lactobacillus species and Pediococcus cerevisiae DMDC has also been shown to be bactericidal against Escherichia coli O157:H7.The antimicrobial effect of DMDC results from the deactivation of microbial enzymes, mainly through reaction with protein imidazole and amine groups, leading to the destruction of the microorganisms. The remaining unreacted DMDC breaks down rapidly into methanol and carbon dioxide. The DMDC activity is based on the hydrolysis rate. Hydrolysis occurs when DMDC reacts with water and the rate is dependent on the temperature of the beverage or wine. It takes about four hours at 10°C (50°F) or two hours at 20°C (68°F) for DMDC completely breaking down.

製法・合成法

純化方法

Dissolve it in Et2O, shake this with a small volume of 0.1N HCl, dry Et2O with Na2SO4 and distil in in vacuo below 100o to give a clear liquid. It decomposes to CO2 and dimethyl carbonate on heating at 123-149o. It is readily hydrolysed by H2O and is a yeast inhibitor and an IRRITANT. [Brysov et al. J Org Chem USSR 10 2551 1974, Boehm & Mehta Chem Ber 71 1797 1938, Beilstein 3 IV 17.]