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リボフラビン

リボフラビン 化学構造式
83-88-5
CAS番号.
83-88-5
化学名:
リボフラビン
别名:
リボフラビン;強力ビスラーゼ;1-デオキシ-1-[3,4-ジヒドロ-7,8-ジメチル-2,4-ジオキソベンゾ[g]プテリジン-10(2H)-イル]-D-リビトール;7,8-ジメチル-10-(1'-D-リビチル)イソアロキサジン;7,8-ジメチル-10-(D-リボ-2,3,4,5-テトラヒドロキシペンチル)-イソアロキサジン;リボデルム;リビプカ;フラバキシン;ホスフラン;ビタミンB2;ベフラビン;ラクトフラビン;7,8-ジメチル-10-(1-デオキシ-D-リビトール-1-イル)ベンゾ[g]プテリジン-2,4(3H,10H)-ジオン;ビタミンG;ビタミン B2(リボフラビン);リボフラビン標準品;ビタミン B2;(−)-リボフラビン;リボフラビン (JP17)
英語化学名:
Riboflavin
英語别名:
Hyre;Q 14;E 101;avine;VIT B2;RibofL;Flaxain;VB2、vb2;RIBIPCA;Ribosyn
CBNumber:
CB4383318
化学式:
C17H20N4O6
分子量:
376.36
MOL File:
83-88-5.mol

リボフラビン 物理性質

融点 :
290 °C (dec.)(lit.)
比旋光度 :
-135 º (c=5, 0.05 M NaOH)
沸点 :
504.93°C (rough estimate)
比重(密度) :
1.2112 (rough estimate)
屈折率 :
-135 ° (C=0.5, JP Method)
闪点 :
9℃
貯蔵温度 :
2-8°C
溶解性:
Very slightly soluble in water, practically insoluble in ethanol (96 per cent). Solutions deteriorate on exposure to light, especially in the presence of alkali. It shows polymorphism (5.9).
外見 :
Powder
酸解離定数(Pka):
1.7(at 25℃)
色:
Yellow to orange
PH:
5.5-7.2 (0.07g/l, H2O, 20°C)
臭い (Odor):
Slight odour
酸塩基指示薬変色域(pH):
6
水溶解度 :
0.07 g/L (20 ºC)
Sensitive :
Light Sensitive
Merck :
14,8200
BRN :
97825
安定性::
Stable, but light-sensitive. Incompatible with strong oxidizing agents, reducing agents, bases, calcium, metallic salts. May be moisture sensitive.
InChIKey:
AUNGANRZJHBGPY-SCRDCRAPSA-N
CAS データベース:
83-88-5(CAS DataBase Reference)
NISTの化学物質情報:
Riboflavine(83-88-5)
EPAの化学物質情報:
Riboflavin (83-88-5)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  F,T
Rフレーズ  11-23/24/25-39/23/24/25
Sフレーズ  24/25-45-36/37-16
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  1
RTECS 番号 VJ1400000
8-10-21
TSCA  Yes
HSコード  29362300
有毒物質データの 83-88-5(Hazardous Substances Data)
毒性 LD50 in rats (g/kg): >10 orally, 5.0 s.c., 0.56 i.p. (Unna, Greslin)
化審法 (5)-3909, (9)-2282 届出不要化学物質
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P307+P311, P321,P405, P501
注意書き
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P311 医師に連絡すること。

リボフラビン 価格 もっと(57)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBQE-6603 リボフラビン
Riboflavin
83-88-5 5g ¥3600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01ACSVIT-002N ビタミンB2
Vitamin B2
83-88-5 1g ¥7400 2021-03-23 購入
東京化成工業 R0020 リボフラビン
Riboflavin
83-88-5 25g ¥3700 2021-03-23 購入
東京化成工業 R0020 リボフラビン
Riboflavin
83-88-5 100g ¥9600 2021-03-23 購入
関東化学株式会社(KANTO) 13235-2A リボフラビン
Riboflavin
83-88-5 100g ¥9900 2021-03-23 購入

リボフラビン MSDS


Riboflavin

リボフラビン 化学特性,用途語,生産方法

外観

赤黄色, 結晶性粉末~粉末

定義

本品は、ビタミンB2であり、次の化学式で表される。

溶解性

水に難溶。エタノール, エーテルに殆ど不溶。アルカリに可溶。水に極めて溶けにくく、エタノールにほとんど溶けない。

解説

7,8-dimethyl-10-D-ribitylisoalloxazine.C17H20N4O6(376.37).ビタミン B2 ともいう.動物の成長促進因子.現在は2-アミノ-4,5-ジメチル-1-リビチルアミノベンゼンとアロキサンとの縮合により生産されている."黄色の結晶性粉末.分解点280 ℃.[α]25D-112°(0.1 mol L-1 水酸化ナトリウム),-122°(水).λmax 220~225,267,374,475 nm(0.1 mol L-1 塩酸).pK1 3.57,pK2 9.50(35 ℃).熱に対して安定であるが,紫外線により強い緑色の蛍光を発して不可逆的に分解し,アルカリ性ではルミフラビンに,中性や酸性ではルミクロムになる.水溶液は黄緑色の蛍光を発し,還元すると無色のロイコフラビンになり,空気にさらして酸化するとふたたびフラビンに戻る.リボフラビンは,アミノ酸オキシダーゼ,NADHデヒドロゲナーゼ,キサンチンオキシダーゼなどでFADまたはFMNの形で補酵素として機能し,細胞呼吸,水素および電子伝達に重要な作用をしている.この欠乏症としては,口唇の障害,口角炎,顔面の局所性脂漏性皮膚炎,特殊な舌炎,眼球機能障害などがある.[CAS 83-88-5]
森北出版「化学辞典(第2版)

用途

光学分割剤。

化粧品の成分用途

皮膚コンディショニング剤

効能

ビタミンB2補充薬

説明

A water-soluble B fraction was found in the 1920s to contain a yellow, fluorescent growth factor called riboflavin in England and vitamin G in the United States. In the early 1930s, several groups found the coenzyme forms of riboflavin 50-phosphate (flavin mononucleotide) and the further conjugate with adenylic acid (flavin adenine dinucleotide).

化学的特性

VITAMIN B2 (Riboflavin). Some earlier designations for this substance included vitamin G, lactoflavin, hepatoflavin, ovoflavin, verdoflavin. The chemical name is 6,7-dimethyl-9-d-l’ribityl isolloxazine. Riboflavin is a complex pigment with a green fluorescence.

化学的特性

Yellow to orange/yellow crystalline powd

物理的性質

Riboflavin is moderately soluble in water (10–13 mg/dl) and ethanol but insoluble in ether, chloroform, and acetone. It is soluble but unstable under alkaline conditions.
The catalytic functions of riboflavin are carried out primarily at positions N-1, N-5, and C-4 of the isoalloxazine nucleus. In addition, the methyl group at C-8 participates in covalent bonding with enzyme proteins. The flavin coenzymes are highly versatile redox cofactors because they can participate in either one- or two electron redox reactions
Riboflavin antagonists include analogs of the isoalloxazine ring (e.g., diethylri boflavin, dichlororiboflavin) and the ribityl side chain (e.g., d-araboflavin, d-galactoflavin, 7-ethylriboflavin).

Originator

Hyflavin ,Endo,US,1948

使用

Vitamin B2 (riboflavin) is produced by yeast from glucose, urea, and mineral salts in an aerobic fermentation.

使用

Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, leafy vegetables. Richest natural source is yeast. Minute amounts present in all plant and animal cells. Vitamin (enzyme cofactor).

使用

Vitamin B2; Vitamin cofactor; LD50(rat) 560 mg/kg ip

使用

riboflavin (Vitamin B2) is used in skin care preparations as an emollient. It can be found in sun care products as a suntan enhancer. Medicinally, it is used for the treatment of skin lesions.

使用

Riboflavin is the water-soluble vitamin b2 required for healthy skin and the building and maintaining of body tissues. it is a yellow to orange-yellow crystalline powder. it acts as a coenzyme and carrier of hydrogen. it is stable to heat but may dissolve and be lost in cooking water. it is relatively stable to storage. sources include leafy vegetables, cheese, eggs, and milk.

定義

ChEBI: D-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl moiety. It is a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vege ables, but the richest natural source is yeast. The free form occurs only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide.

Manufacturing Process

100 g of riboflavin and 3 of potassium carbonate are suspended in 500 cc of the aqueous formaldehyde solution and the mixture is stirred at 30°C for 8 hours. At the end of this period, 5 cc of glacial acetic acid and 1 liter of methanol are added, with stirring. The solution is freed from undissolved material by filtration and the clear solution is poured slowly at about 20°C to 22°C with vigorous stirring into 8 liters of anhydrous acetone. The resultant precipitate is filtered off, washed repeatedly with anhydrous acetone and with ether, and then dried at room temperature and with vacuum. The resultant dried powder is dissolved in hot water at 95°C to give an aqueous solution of 20% by weight. This solution is kept in the dark at room temperature for 3 to 4 weeks, after which time a large amount of material crystallizes out of the solution. This crystallized material is removed by filtration and recrystallized from hot water. A small amount of dark red insoluble material is filtered from the hot solution. This recrystallization step is repeated four times. The resultant end product is monomethylol riboflavin, which crystallized in small orange clusters. It has a melting point of 232°C to 234°C with decomposition, and it becomes dark when heated above 225°C.

brand name

Flavaxin (Sterling Winthrop).

Therapeutic Function

Enzyme cofactor vitamin source

一般的な説明

The conflicting results were eventually found to be due,in part, to deficiencies in study animals not just of vitamin B2,but also vitamin B3 (niacin), the cause of human forms of pellagra,and/or vitamin B6 (pyridoxine), another cause of dermatitis.Likewise, treatments with vitamin B2 were inconsistentbecause the early sources of this vitamin contained otherB vitamins. Vitamin B2 was eventually isolated from eggwhites in 1933 and produced synthetically in 1935. Thename riboflavine was officially accepted in 1960; althoughthe term was in common use before then. In 1966, IUPACchanged it to riboflavin, which is in common use today.Riboflavin is synthesized by all green plants and by mostbacteria and fungi. Therefore, riboflavin is found, at least insmall amounts, in most foods. Foods that are naturally highin riboflavin include milk and other dairy products, meat,eggs, fatty fish, and dark green vegetables.
Chemically, riboflavin is an N-glycoside of flavin, alsoknown as lumichrome, and the sugar, ribitol .Flavin is derived from the Latin word flavus for “yellow”because of the yellow color of its crystals and yellow fluorescenceunder UV light. Riboflavin is heat stable but easilydegraded by light. Its systematic names are 7,8-dimethyl-10-ribitylisoalloxazine and 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine.

Biochem/physiol Actions

Riboflavin serves as a precursor for the active enzyme cofactors riboflavin 5′-monophosphate (also called flavin mononucleotide or FMN) and flavin adenine dinucleotide (FAD). Riboflavin deficiency in the diet results in a well-defined syndrome known as ariboflavinosis, Riboflavin exhibits protective effects against tumor development and cardiovascular disease. Its deficiency often affects metabolism involving redox reactions. Riboflavin is found essential for iron absorption, gastrointestinal development, neurogenesis, corneal vascularization and corneal opacity.

臨床応用

Severe riboflavin deficiency is known as ariboflavinosis, andtreatment or prevention of this condition is the only provenuse of riboflavin. Ariboflavinosis is most commonly associatedwith multiple vitamin deficiency as a result of alcoholismin developed countries. Because of the large numberof enzymes requiring riboflavin as a coenzyme, deficienciescan lead to a wide range of abnormalities. In adults seborrheicdermatitis, photophobia, peripheral neuropathy, anemia, andoropharyngeal changes including angular stomatitis, glossitis,and cheilosis, are often the first signs of riboflavin deficiency.In children, cessation of growth can also occur. As the deficiencyprogresses, more severe pathologies develop untildeath ensues. Riboflavin deficiency may also produce teratogeniceffects and alter iron handling leading to anemia.

安全性プロファイル

Poison by intravenous route. Moderately toxic by intraperitoneal and subcutaneous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

環境運命予測

Physicochemical Properties
Riboflavin has the appearance of a yellow to orange amorphous solid and imparts an orange color to the B vitamin tablets. Riboflavin has a melting point of 290°C, a density of 1.65, and a refractive index of 135°. The pKa is 9.888 and log P is 0.095. Riboflavin has solubility in water of 0.1 g l-1.
Exposure Routes and Pathways
The route of exposure is oral. Dietary sources of riboflavin and its coenzymes include broccoli, spinach, asparagus, enriched flour, yeast, eggs, milk, cheese, mackerel, trout, poultry, liver, and kidneys.
Toxicokinetics
Riboflavin, which is only moderately water soluble, is absorbed from the gastrointestinal tract but is limited to about 27 mg at any one time from an oral dose given to an adult. Hence, mega doses would not be expected to increase significantly the total amount absorbed. It is hepatically metabolized, protein bound, and widely distributed to tissue; however, little is stored in the liver, spleen, heart, and kidneys. Riboflavin is excreted renally as metabolites, which have been oxidatively cleaved in the ribityl side chain and converted to hydroxymethyls in the ring methyl functions. Riboflavin in excess of daily body needs is excreted unchanged in the urine. Riboflavin exhibits biphasic pharmacokinetics with initial and terminal half-lives of 1.4 and 14 h, respectively.

Properties and Applications

yellow

純化方法

It crystallises from H2O as a yellow-orange powder in three different forms with differing amounts of H2O. It melts if placed in an oil bath at 250o, but decomposes at 280o if heated at a rate of 5o/minute. It is also purified by crystallisation from 2M acetic acid, then extracted with CHCl3 to remove lumichrome impurity. [Smith & Metzler J Am Chem Soc 85 3285 1963.] Its solubility in H2O is 1g in 3-15L depending on the crystal structure. Its solubility in EtOH at 25o is 4.5mg in 100mL. Store it in the dark because it is decomposed to lumichrome by UV light. [Pearson The Vitamins vol V pp1-96 1967 and vol VII pp 1-96 1972, Gy.gy and Pearson eds, Academic Press, Beilstein 26 IV 2542.]

リボフラビン 上流と下流の製品情報

原材料

準備製品


リボフラビン 生産企業

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83-88-5(リボフラビン)キーワード:


  • 83-88-5
  • vitasanb2
  • xypentyl)-
  • E 101
  • Riboflavin (1.07609)
  • Riboflavin Vitamin B2
  • Vitamin B2 (Riboflavine)
  • RIBOFLAVIN DC GRADE
  • RIBOFLAVIN USP (VITAMIN B-2)
  • RIBOFLAVIN USP,GRANULATED
  • RIBOFLAVIN CELL CULTURE TESTED
  • RIBOFLAVIN ELECTROPHORESIS REAGENT
  • RIBOFLAVINE BIOSYNTH
  • LACTOFLAVIN PH EUR
  • RIBOFLAVIN USP
  • RIBOFLAVIN PLANT CELL CULTURE TESTED
  • RIBOFLAVIN (B2), 1000MG, NEAT
  • RiboflavinForBiochemistry99%
  • Riboflavin80%
  • RIBOFLAVIN FOR BIOCHEMISTRY
  • RIBOFLAVIN FOR BIOCHEMISTRY 99%
  • Riboflavin Bp
  • Riboflavin (non-medicinal)
  • Vitamin B2
  • riboflavin (b2)
  • Riboflavin (500 mg) (Vitamin B2)
  • VITAMIN B2(RIBOFLAVIN)(SH)
  • Riboflavin-[13C4,15N2] (Vitamin B2)
  • RIBOFLAVIN,FCC
  • RIBOFLAVIN,REAGENT
  • 7,8-dimethyl-10-[(2R,3R,4S)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
  • リボフラビン
  • 強力ビスラーゼ
  • 1-デオキシ-1-[3,4-ジヒドロ-7,8-ジメチル-2,4-ジオキソベンゾ[g]プテリジン-10(2H)-イル]-D-リビトール
  • 7,8-ジメチル-10-(1'-D-リビチル)イソアロキサジン
  • 7,8-ジメチル-10-(D-リボ-2,3,4,5-テトラヒドロキシペンチル)-イソアロキサジン
  • リボデルム
  • リビプカ
  • フラバキシン
  • ホスフラン
  • ビタミンB2
  • ベフラビン
  • ラクトフラビン
  • 7,8-ジメチル-10-(1-デオキシ-D-リビトール-1-イル)ベンゾ[g]プテリジン-2,4(3H,10H)-ジオン
  • ビタミンG
  • ビタミン B2(リボフラビン)
  • リボフラビン標準品
  • ビタミン B2
  • (−)-リボフラビン
  • リボフラビン (JP17)
  • 生化学
  • ビタミン
  • ビタミンB群
  • 代謝作用薬
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