기본 정보
- 표준 SMILES
O.O.O=C(O)C(=O)O- InChIKey
GEVPUGOOGXGPIO-UHFFFAOYSA-N- 분자식
- C2H2O4.2H2O
- 평균 분자량
- 126.07 g/mol
- 단동위원소 질량
- 126.01643791
개요
Oxalic acid is a dicarboxylic acid. It is a colorless crystalline solid that dissolves in water to give colorless, acidic solutions. In terms of acid strength, it is much stronger than acetic acid. Oxalic acid, because of its di-acid structure can also act as a chelating agent for metal cations. About 25% of produced oxalic acid is used as a mordant in dyeing processes. It is also used in bleaches, especially for pulpwood. Oxalic acid's main applications include cleaning (it is also found in baking powder) or bleaching, especially for the removal of rust. Oxalic acid is found in a number of common foods with members of the spinach family being particularly high in oxalates. Beat leaves, parsley, chives and cassava are quite rich in oxalate. Rhubarb leaves contain about 0.5% oxalic acid and jack-in-the-pulpit (Arisaema triphyllum) contains calcium oxalate crystals. Bacteria naturally produce oxalates from the oxidation of carbohydrates. At least two pathways exist for the enzyme-mediated formation of oxalate in humans. In one pathway, oxaloacetate (part of the citric acid cycle) can be hydrolyzed to oxalate and acetic acid by the enzyme oxaloacetase. Oxalic acid can also be generated from the dehydrogenation of glycolic acid, which is produced by the metabolism of ethylene glycol. Oxalate is a competitive inhibitor of lactate dehydrogenase (LDH). LDH catalyses the conversion of pyruvate to lactic acid oxidizing the coenzyme NADH to NAD+ and H+ concurrently. As cancer cells preferentially use aerobic glycolysis, inhibition of LDH has been shown to inhibit tumor formation and growth. However, oxalic acid is not particularly safe and is considered a mild toxin. In particular, it is a well-known uremic toxin. In humans, ingested oxalic acid has an oral lowest-published-lethal-dose of 600 mg/kg. It has been reported that the lethal oral dose is 15 to 30 grams. The toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate, the main component of kidney stones. Oxalic acid can also cause joint pain due to the formation of similar precipitates in the joints.
이름 및 식별자
- 우선 이름
- Oxalic acid dihydrate
- IUPAC
- oxalic acid;dihydrate
- 현지명
- 옥살산
- 영어명
- Oxalic acid dihydrate
- 분자식
- C2H6O6
- 분자량
- 126.07
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
6153-56-6- PubChem CID
- 61373
- DTXSID
DTXSID2075003- ChEMBL
CHEMBL5315063- UNII
- 0K2L2IJ59O
- EC Number
- 612-167-2
물성
구조 계산 물성
- 극성 표면적
- 76.6 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 8
- 형식 전하
- 0
- 복잡도
- 71.5
실험 및 물리화학적 성질
Density
1.65 g/cm³
1.653 @25 °C
Animal Drugs
EMA approved medicines: Veterinary medicine
EMA approved medicines: Veterinary medicine
Melting Point
101-102 °C
189.5 °C
Physical Description
Large Crystals; Dry Powder; Other Solid; Liquid; Liquid; Other Solid
Colorless solid; [ICSC] Colorless hygroscopic crystals; [Sigma-Aldrich MSDS]
COLOURLESS CRYSTALS.
물리화학적 성질
- 녹는점
- 104 · 104-106 °C(lit.)
- 끓는 점
- 108 · 108-109°C
- 밀도
- 1 · 1,65 g/cm3
- 증기 밀도
- 4.4 · 4.4 (vs air)
- 증기압
- 0.01 mm · <0.01 mm Hg ( 20 °C)
- 인화점
- 157 °C · 157°C
- 저장 조건
- 5 °C · Store at +5°C to +30°C.
- 용해도
- 2 O: · H2O: 20°C에서 용해성 1M, 투명, 무색
- 물리적 상태
- 분말/고체
- Specific Gravity
- 1.65 · 1.65
- 색상
- 노란색에서 노란색-녹색
- 수소이온지수(pH)
- 1 · ~1.0 (25℃, 1M in H2O)
- 수용성
- 138 g/L · 138g/L(20℃)
- Merck
- 14 · 14,6911
- BRN
- 3679436 · 3679436
- 안정성
- 안정적인. 염기, 산 염화물, 강철, 은, 은 화합물, 습기와 호환되지 않습니다. 금속과의 접촉을 피하십시오.
- InChI
- 1S/C2H2O4.2H2O/c3-1(4)2(5)6;;/h(H,3,4)(H,5,6);2*1H2
- InChIKey
- GEVPUGOOGXGPIO-UHFFFAOYSA-N
- SMILES
- [H]O[H].[H]O[H].OC(=O)C(O)=O
- NIST
- Oxalic acid dihydrate(6153-56-6)
- EPA
- Oxalic acid dihydrate (6153-56-6)
- Absorption
- 303 nm · cut-off at 303nm in H2O at 1M
화학적 성질
Oxalic acid dihydrate occurs as colorless crystals or a white crystalline powder; it is odorless. It sublimes at 150–160 °C and effloresces in warm, dry air. One gram is soluble in 7 mL of water, 2 mL of boiling water, 2.5 mL of ethanol, 1.8 mL of boiling ethanol, 100 mL of diethyl ether, and 5.5 mL of glycerol; it is insoluble in benzene, chloroform, and petroleum ether. The pH of a 0.1 mol/L solution is 1.3. It has low toxicity; (rabbit, dermal) is 2000 mg/kg.
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 1.1% (6 of 561) of reports.
Danger
H302+H312 (12.7%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]
P260, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 561 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
유해성 정보
Regulatory Information
Chemical: Ethanedioic acid, dihydrate
Ethanedioic acid, dihydrate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanedioic acid, dihydrate are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Oxalic acid dihydrate: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes burns; Ingestion may have effects on calcium balance; Repeated or prolonged exposure may cause kidney stones; [ICSC] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion and skin absorption; May have teratogenic effects; Targets the kidney, nerves, blood, and eyes; [Sigma-Aldrich MSDS] See Oxalic acid.
Chemical Dangers
Decomposes on contact with hot surfaces or flames. This produces formic acid and carbon monoxide. The solution in water is a medium strong acid. Reacts violently with strong oxidants. This generates fire and explosion hazard. Reacts with some silver compounds. This produces explosive silver oxalate. Attacks some forms of plastic.
Hazard Classes and Categories
Acute Tox. 4 (98.8%)
Acute toxicity - category 4
안전 및 보호
First Aid Measures
Fresh air, rest. Half-upright position. Refer immediately for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Refer for medical attention .
Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.
Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance, protective gloves and safety goggles. Sweep spilled substance into covered plastic containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.
Threshold Limit Values (TLV)
1.0 [mg/m3]
2.0 [mg/m3]
1 mg/m
독성 정보
Treatment
Acute Exposure: If oxalic acid is swallowed, immediately give the person water or milk, unless instructed otherwise by a health care provider. DO NOT give water or milk if the person is having symptoms (such as vomiting, convulsions, or a decreased level of alertness) that make it hard to swallow. If acute exposure occurs to the eyes, irrigate opened eyes for several minutes under running water. Chronic exposure: in some patients with primary hyperoxaluria type 1, pyridoxine treatment (vitamin B6) may decrease oxalate excretion and prevent kidney stone formation.
Health Effects
Because it binds vital nutrients such as calcium, long-term consumption of foods high in oxalic acid can be problematic. Healthy individuals can safely consume such foods in moderation, but those with kidney disorders, gout, rheumatoid arthritis, or certain forms of chronic vulvar pain (vulvodynia) are typically advised to avoid foods high in oxalic acid or oxalates. The calcium oxalate precipitate (better known as kidney stones) obstruct the kidney tubules. Conversely, calcium supplements taken along with foods high in oxalic acid can cause calcium oxalate to precipitate out in the gut and drastically reduce the levels of oxalate absorbed by the body (by 97% in some cases.) Chronically high levels of oxalic acid are associated with at least 2 inborn errors of metabolism including: Type I primary hyperoxaluria and Primary hyperoxaluria. Oxalate stones in primary hyperoxaluria tend to be severe, resulting in relatively early kidney damage (before age 20), which impairs the excretion of oxalate leading to a further acceleration in accumulation of oxalate in the body. After the development of renal failure patients may develop oxalate deposits in the bones, joints and bone marrow. Severe cases may develop haematological problems such as anaemia and thrombocytopaenia. The deposition of oxalate in the body is sometimes called "oxalosis" to be distinguished from "oxaluria" which refers to oxalate in the urine.
Toxicity Summary
The affinity of divalent metal ions is sometimes reflected in their tendency to form insoluble precipitates. Thus in the body, oxalic acid also combines with metals ions such as Ca2+, Fe2+, and Mg2+ to deposit crystals of the corresponding oxalates, which irritate the gut and kidneys. (2) Therefore the toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate, the main component of kidney stones. Oxalic acid can also cause joint pain due to the formation of similar precipitates in the joints. Ingestion of ethylene glycol results in oxalic acid as a metabolite that can also cause acute kidney failure.
Signs and Symptoms
Cough. Sore throat. Burning sensation. Shortness of breath. Laboured breathing. Headache.
Redness. Pain. Skin burns.
Redness. Pain. Blurred vision. Burns.
Sore throat. Burning sensation. Abdominal pain. Laboured breathing. Convulsions. Paralysis. Cardiac dysrhythmia. Shock or collapse.
Oxalic acid poisoning symptoms include weakness, burning in the mouth, death from cardiovascular collapse, on the respiratory system, throat – burning in the throat, abdominal pain, nausea, vomiting, diarrhea, convulsions, and coma.
안전 데이터
- wgk
- 1
- tsca
- Yes
- rtecs
- RO2450000
- ridadr
- UN 3261 8/PG 3
- 독성
- LD50 orally in Rabbit: 375 mg/kg
- HS 번호
- 29171100
- risk_code
- 21/22-41
- hazard_code
- Xn,C
- safety_code
- 24/25-39-37-36-26
- 포장분류
- III
- 위험 등급
- 8
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
용도 및 제조
Uses
Used in calico printing and dyeing, bleaching straw hats and leather, cleaning wood and metals, purifying methanol, decolorizing crude glycerol, stabilizing hydrocyanic acid, removing paint, and removing stains; Also used in ceramics and pigments, in veterinary hemostatic solutions, in blood specimen anticoagulants, and in other industries (paper, photography, engraving, and rubber manufacturing); [Merck Index] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
Pulp and Paper Processing [Category: Industry]
Oxalic acid and oxalates are abundantly present in many plants, most notably fat hen (lamb's quarters), sorrel, and Oxalis species. The root and/or leaves of rhubarb and buckwheat are listed being high in oxalic acid.[8] Other edible plants that contain significant concentrations of oxalic acid include—in decreasing order—star fruit (carambola), black pepper, parsley, poppy seed, amaranth, spinach, chard, beets, cocoa, chocolate, most nuts, most berries, and beans. (L618)
응용 분야
용도Oxalic acid dihydrate is a purifying agent in pharmaceutical industry, special in antibiotic medication, such as Oxytetracycline , Chloramphenicol , etc; * Precipitating agent in Rare-earth mineral processing; * Bleaching agent in the textile activities, wood pulp bleaching; * Rust-remover for Metal treatment; * Grinding agent, such as Marble polishing; * Waste water treatment, removing calcium from water.
일반 설명Oxalic acid dihydrate (OAD) crystals are reported to be monoclinic with P21/n space group. The electron density of OAD has been obtained using X-ray diffraction studies under high resolution.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
순도시험(1) 용상 : 이 품목 1g에 물 20mL를 가하여 끓여 녹일 때, 그 액은 무색으로서 탁도는 거의 징명 이하이어야 한다. (2) 황산염 : 이 품목 1g에 물 20mL 및 탄산나트륨시액 1mL를 가하고 수욕상에서 증발건고한 다음 천천히 가열하고 다시 600~700℃로 강열한다. 이 잔류물에 물 10mL 및 질산 0.5mL를 가하여 끓이고 다시 염산 2mL를 가하여 수욕상에서 증발건고한 다음 그 잔류물에 물을 가하여 100mL로 하고 여과하여 여액 25mL를 취해서 묽은염산 1mL를 가한 것을 시험용액으로 하여 황산염시험법에 따라 시험할 때, 그 양은 0.01N 황산 0.4mL에 대응하는 양 이하이어야 한다. (3) 비소 : 이 품목을 비소시험법에 따라 시험할 때, 그 양은 4.0ppm 이하이어야 한다. (4) 납 : 이 품목 5.0g을 취하여 원자흡광광도법 또는 유도결합플라즈마발광광도법에 따라 시험할 때, 그 양은 2.0ppm 이하이어야 한다.
정량법이 품목 약 1g을 정밀히 달아 물에 녹여 250mL로 하고 그 중 50mL에 황산 3mL를 가하여 약 80℃로 가열하여 뜨거울 때 0.1N 과망간산칼륨용액으로 적정한다.0.1N 과망간산칼륨용액 1mL = 6.304mg C2H2O4•H2O
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