ヘスペリジン 化学特性,用途語,生産方法
外観
白色～淡褐黄色の結晶性の粉末又は粉末
定義
本品は、レモンやスイートオレンジ等に存在する主要なフラボノイドであり、次の化学式で表される。
溶解性
水酸化ナトリウム溶液に溶け、水、エタノール及びジエチルエーテルにほとんど溶けない。エーテル、ベンゼンに不溶。クロロホルム、アセトン、水に難溶。メタノールに微溶。熱酢酸、アニリンにやや易溶。
解説
ヘスペリジン．フラバノンのルチノース配糖体．かんきつ類のほとんどすべて，とくに未熟な外果皮に含まれる．白色の微小針状晶．融点258～262 ℃．[α]20D－76°(ピリジン)．希アルカリ水溶液，アニリン，ピリジン，熱酢酸に可溶，メタノールに微溶，エーテル，ベンゼンに不溶．いわゆるビオフラボノイドとしてビタミンPとよばれるものの一つで，毛細血管強化薬に用いられる．
用途
ビタミンPの一つで、毛細血管の保護に用いられる。
化粧品の成分用途
香味剤
効能
血管保護薬
使用上の注意
不活性ガス封入
説明
Hesperidin exists mainly in the peel of lemon, orange, and Seville orange flower,
which belong to facilitating medicine. These Chinese medicines are warm and fragrant with the function of eliminating depression and knots. They cure abdominal
distension, belching swallow acid pain, nausea and vomiting, diarrhea or constipation caused by the spleen, and stomach qi zhi; and they also cure depression, hernia,
breast pain, and menoxenia caused by liver qi; moreover, they cure chest pain,
cough, and asthma, which are caused by lung qi.
Modern research has shown that li qi medicines have an extensive effect, such as
regulatory effect on the digestive system, and they control the bronchial smooth
muscle, the uterus smooth muscle, and the cardiovascular system. The base of the
effect of li qi medicines in inverse, anti-nausea, antidiarrheal, and analgesia pharmacological effects is its effect in inhibiting gastric bowel movement; its exciting gastrointestinal movement is the foundation to eliminate swelling; its effect in relaxation
of the bronchial smooth muscle is the foundation of pharmacological effects in antinausea. The intravenous injection to treat shock effect is the new development of li
qi medicine.
化学的特性
light brown powder
物理的性質
Appearance: fine dendritic crystal (precipitation at pH 6–7), odorless, tasteless.
Melting point: 258–262?°C (softening at 250?°C). Solubility: 1?g of hesperidin can be
soluble in 50?l of water. Hesperidin dissolves in dimethyl formamide and formamide
at 60?°C.?It is slightly soluble in methanol and hot ice acetic acid and hardly soluble
in acetone, benzene, and chloroform and is soluble in dilute alkali and pyridine.
来歴
Hesperidin is the glycoside in the form of hesperidin and rubiose and is a derivative
of dihydroflavonoids. It widely exists in legume, birch, lip flower, butterfly flower,
Rutaceae, and citrus plants. Hesperidin is an important composition of citrus
pulp and peel; most of hesperidin exists in citrus processing waste such as skin and
fruit bag. Mature skin and tissue have the highest content of hesperidin (30–50% in
endocarp; 30–50% in orange collaterals, nuclear, and pulp; and 10–20% in exo_x005fcarp); the content of hesperidin is relatively low in juice and orange bag, which is
about 1–5%. The crude extracts of hesperidin was first discovered in 1827 by
Lebreton. Then the Hungarian scholar Albert Szent-Gyorgi discovered that the flavonoids have a protective microvascular effect in 1936, which is similar to that of
vitamin P. Preparation of vitamin P was made in 1938. It was not until 1949
that it was discovered that vitamin P was made up of two flavonoids, luteolin and
hesperidin, which are believed to be vitamin active. This substance, which was later
named as vitamin P, was designed to reduce blood vessel permeability and brittleness, as well as alleviate bad blood and vitamin C deficiency. It was later discovered
that the substance had an antioxidant effect, so the name of vitamin P was abandoned. Due to the widespread distribution of hesperidin in plant medicine, the
research and development have been widely followed.
使用
Hesperidin is a flavoring agent that is a bioflavonoid found in citrus
pulp. it has minor use as a flavorant.
定義
ChEBI: A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
適応症
Hesperidin can be used for cardiovascular disease prevention and treatment, blood
sugar and blood lipid and blood pressure regulation, circulatory system regulation,
and body regulation, and it can also be used as an antibacterial, anti-inflammatory,
and antiviral.
薬理学
The pharmacological effect of hesperidin is widespread, and people thought it was
vitamin P in the early days, but in recent years, people found that it has other functions such as controlling blood pressure, antiallergic, reducing bone mineral density
and cholesterol, improving enzyme activity and microcirculation, antibacterial,
anti-inflammatory, anti-hepatitis B, antitumor, and other pharmacological effects.Hesperidin has the function of vitamin P, which can reduce capillary permeability and prevent microvascular hemorrhage. Intraperitoneal injection of hesperidin at
175–250?mg/kg in mice could increase permeability of blood vessels by antihistamine and inhibiting hemolytic lecithin. Hesperidin has antiviral and antimicrobial
effect, and preincubation with hesperidin at 200? mg/ml protects the cells from
viruses. One to 10?μg/ml of hesperidin effectively inhibits the growth of the fungus.
It has the effect of maintaining the normal osmotic pressure of the blood vessels,
reducing the shortness of blood vessels, shortening bleeding time, reducing blood
fat, and preventing atherosclerosis; hesperidin has an effect on the gastrointestinal
tract, which can excite the smooth muscle transiently and then inhibit it, and it is a
major component of the diet drug; hesperidin has an effect of anti-lipid peroxidation
and scavenging hydroxyl radical. Hesperidin is a newly discovered flavonoid compound which has an effect in the central nervous system; it has a sedative effect. At
the same time, hesperidin has the effect of lowering cholesterol, curing rheumatism,
and inhibiting skin pigmentation. Hesperidin is a strong affinity for estrogen receptors, which can be used in estrogen receptors to prevent bone loss and reduce the
number of osteoblasts.
Hesperidin has a significant inhibitory effect on human lung
cancer, colorectal cancer, kidney cancer, and human breast cancer cells, which can
be used for cancer prevention.
臨床応用
Hesperidin has the effect to maintain osmotic pressure, strengthen the capillary
toughness, shorten the bleeding time, lower cholesterol, and so on. Although hesperidin cannot be used as independent medication, it is recorded in the pharmacopoeia that hesperidin, as auxiliary materials, is widely used to aid in the treatment
of cardiovascular system; it can be configured as a variety of drugs to prevent hardening of the arteries and myocardial infarction. It is one of the main raw materials
of medicine “pulse.” Hesperidin is used as auxiliary materials for the treatment of
vascular brittleness, bedsore, rheumatoid arthritis, vitamin C deficiency disease,
trauma, obstetric disease, gum inflammation, edema, and gastrointestinal tract disease in the world. Hesperidin can be used to produce an anticancer drug called
diosmin. Natural antioxidant is available in the food industry. It is also used in
the cosmetics industry.
副作用
Potential side effects of hesperidin include: abdominal pain, diarrhoea, nausea, contact dermatitis (itchy rash caused by direct contact with the substance). In a study evaluating the effects of hesperidin supplementation on heart attacks, no serious adverse reactions were reported.
純化方法
Dissolve hesperidine in dilute aqueous alkali and precipitate it by adjusting the pH to 6-7. [Beilstein 18 III/IV 3219, 18/5 V 218.]
ヘスペリジン 上流と下流の製品情報
原材料
準備製品
β-フェニルプロピオフェノン
ETHYL LINOLEATE
(2S)-2-(3,4-dimethoxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
ジオスミン