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메나디온 구조식 이미지
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포뮬러 무게:
MOL 파일:

메나디온 속성

105-107 °C(lit.)
끓는 점
262.49°C (rough estimate)
1.1153 (rough estimate)
1.5500 (estimate)
저장 조건
room temp
oil: soluble
물리적 상태
Slight odor
Light Sensitive
Stable. May be light sensitive. Incompatible with strong oxidizing agents.
CAS 데이터베이스
58-27-5(CAS DataBase Reference)
Menadione (58-27-5)
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,Xi
위험 카페고리 넘버 22-36/37/38-43
안전지침서 26-36-37/39-24
WGK 독일 3
RTECS 번호 QL9100000
F 고인화성물질 8
HS 번호 29147000
유해 물질 데이터 58-27-5(Hazardous Substances Data)
독성 LD50 orally in mice: ~0.5 g/kg (Molitor, Robinson)
유해화학물질 필터링 2018-1-835(신규화학물질)
함량 및 규제정보 물질구분: 유독물질; 혼합물(제품)함량정보: 2-메틸-1,4-나프탈렌디온 및 이를 25% 이상 함유한 혼합물
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.
NFPA 704
2 1

메나디온 C화학적 특성, 용도, 생산

화학적 성질

Bright yellow crystals

물리적 성질

Appearance: phylloquinone is a yellow oil at room temperature, but the other vitamers K are yellow crystals. Solubility: the vitamers K and MK and most forms of menadione are insoluble in water, slightly soluble in ethanol, and readily soluble in ether, chloroform, fats, and oils. Stability: the vitamers K are sensitive to light and alkali, but are relatively stable to heat and oxidizing environments.
Menadione, the formal parent compound of the menaquinone series does not occur naturally but is a common synthetic form called menadione (2-methyl-1,4- naphthoquinone). This compound forms a water-soluble sodium bisulfite addition product, menadione sodium bisulfite, whose practical utility is limited by its instability in complex matrices such as feeds. However, in the presence of excess sodium bisulfite, it crystallizes as a complex with an additional mole of sodium bisulfite (i.e., menadione sodium bisulfite complex), which has greater stability, therefore, is used widely as a supplement to poultry feeds. A third water-soluble compound is menadione pyridinol bisulfite (MPB).


Kappaxin,Sterling Winthrop


Precursor to verious types of Vitamin K. Used as a micronutrient for livestock and pet foods.


prothrombogenic agent




The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.


vitamin K helps promote blood clotting and has been used medically to reduce the possibility of bruising after surgery. It is being incorporated into cosmetic preparations, particularly those used for treating dark circles. It could also be used in acne products, and there are studies underway on its efficacy for the treatment of spider veins.


Menadione (Vitamin K) is a fat-soluble vitamin that is essential for blood clotting. It is destroyed by irradiation during processing but has no appreciable loss during storage. It occurs in spinach, cabbage, liver, and wheat bran.


Vitamin K activity is associated with several quinones, including phylloquinone (vitamin K1), menadione (vitamin K3), and a variety of menaquinones (vitamin K2). These quinones promote the synthesis of proteins that are involved in the coagulation of blood.These proteins include prothrombin, factor VII (proconvertin), factor IX (plasma thromboplastin). The vitamin K quinones are obtained from three major sources.Vitamin K is present in various plants, especially green vegetables. The menaquinones that possess vitamin K2 activity are synthesized by bacteria, particularly gram-positive organisms; the bacteria in the gut of animals produce useful quantities of this vitamin.Vitamin K3 is a chemically synthesized quinone that possesses the same activity as vitamin K1.


ChEBI: A member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group.

Manufacturing Process

Dissolve 100 g of β-methylnaphthalene in 500 g of carbon tetrachloride. Dissolve 500 g of commercial sodium dichromate in 175 g of hot water. Pour these two solutions into a 3-liter 3-necked flask, equipped with an efficient stirrer, a reflux condenser, and a dropping funnel. The flask should be put into a water bath held at 50°C. The contents of the flask agitated as violently as possible at adding (through the dropping funnel) 896 g of 77% (by weight) sulfuric acid. The rate of dropping depends on the efficiency of the reflux condenser. If the reaction tends to get out of hand due to overheating, cold water should be run into the water bath. After the addition of acid has been completed, keep the water bath at 70°C, for 1% to 2 hours. Then stop the agitation, cool the mixture and decant therefrom as much of the carbon tetrachloride layer as possible. Pour water into the flask; add 100 g more of carbon tetrachloride and stir for an additional ten minutes. The carbon tetrachloride layer will now settle to the bottom. The acid layer can be decanted and discarded, or worked up for those components desired. A complete separation of the acid from the carbon tetrachloride is effected by means of a separatory funnel. All of the carbon tetrachloride solutions are pooled and filtered to clarity through filter paper. The carbon tetrachloride may be distilled off from the quinone in a vacuum, using a water bath heated to 50°C.
The quinone is concentrated to a point where crystallization begins. Thereupon the concentrated solution is transferred to a beaker and allowed to crystallize at room temperature. Further crops of crystals are obtained by allowing the mother liquor to cool in an icebox, or by reducing it still further. If the β-methylnaphthalene starting material was pure, the 2-methyl-1,4- naphthoquinone obtained will have a melting point of 100°-104°C, without further purification. Vacuum sublimation has been found most effective to produce quinones of a very high purity. There is a rapid method of oxygenation of β-methylnaphthalene: 3 g of β-methylnaphthalene is dissolved in 180 grams of carbon tetrachloride. To this is added 15 grams of commercial sodium dichromate dissolved in 6 grams of hot water. The above solutions are placed in a 1-liter 3-necked flask equipped with an efficient stirrer, a dropping funnel, and a distilling condenser of large bore. The mixture is agitated energetically, and 25 grams of 77% sulfuric acid added through the dropping funnel. The time of addition need not be over 30 seconds. The flask is not subjected to exterior cooling, as the distilling carbon tetrachloride should hold the heat to the proper temperature, which should not exceed 85°C. After five minutes the reaction may be discontinued and the product handled similarly to the method outlined in above. The yield of 2-methyl-1,4-naphthoquinone will be around 80% of theoretical by the use of this rapid method.


Kappaxin (Sterling Winthrop); Kayquinone.

Therapeutic Function

Prothrombogenic vitamin


Irritant to skin and mucous membranes, especially the alcoholic solution.


The typical role of vitamin K is to maintain normal blood coagulation function. Its role is related to the metabolic processes.

Clinical Use

Vitamin K deficiency results in increased bleeding time. This hypoprothrombinemia may lead to hemorrhage from the gastrointestinal tract, urinary tract, and nasal mucosa. In normal, healthy adults, deficiency is rare. The two groups at greatest risk are newborn infants and patients receiving anticoagulant therapy; hypoprothrombinemia preexists in these two groups. Any disease that causes the malabsorption of fats may lead to deficiency. Inhibition of the growth of intestinal bacteria from extended antibiotic therapy will result in decreased vitamin K synthesis and possible deficiency.


Toxicity of vitamin K has not been well defined. Jaundice may occur in a newborn if large dosages of vitamin K are given to the mother before birth. Although kernicterus may result, this can be prevented by using vitamin K.

Safety Profile

Poison by ingestion, intraperitoneal, and subcutaneous routes. Experimental teratogenic effects. Questionable carcinogen with experimental tumorigenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Recrystallise it from 95% EtOH, or MeOH after filtration. It forms bright yellow crystals which are decomposed by light. Its solubility in EtOH is 1.7% and in *C6H6 it is 10%. It IRRITATES mucous membranes and skin. [Fieser J Biol Chem 133 391 1940, Beilstein 7 IV 2430.]

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