Hesperetin-7-Rutinoside

HCID 3594

Basic information

CAS
520-26-3
Standard SMILES
COc1ccc(C2CC(=O)c3c(O)cc(OC4OC(COC5OC(C)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2)cc1O
InChIKey
QUQPHWDTPGMPEX-UHFFFAOYSA-N
Molecular formula
C28H34O15
Average molar mass
610.6 g/mol
Monoisotopic mass
610.18977037

Names & identifiers

Preferred name
Hesperetin-7-Rutinoside
IUPAC
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
English name
Hesperidin
Molecular formula
C28H34O15
Molecular weight
610.56

Names & synonyms

Hesperetin-7-rutinosideRefChem:1086470Hesperidin, (2S)-USAF CF-3Hesperidin, (S)-(-)-Hesperitin-7-rhamnoglucosideHesperedinAtripliside B5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{3,4,5-trihydroxy-6-[(3,4,5-trihydro xy-6-methyl(2H-3,4,5,6-tetrahydropyran-2-yloxy))methyl](2H-3,4,5,6-tetrahydrop yran-2-yloxy)}chroman-4-oneHesperetin-7-O-rutinoside5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranosideC28H34O15
Show more names
HESPERIDINEVITAMIN PCitrus Sinensis Extract(s)-7-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-oneHesperidenHespiridin(S)-7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-oneHesperidHespeidin
NSC 44184Hesperetin, 7-(6-O-(6-deoxy-.alpha.-L-mannopyranosyl))-.beta.-D-glucopyranoside)Hesperetin, 7-[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)]-.beta.-D-glucopyranoside)Hesperidin [M+H]+Usaf cf-3 f1 gluco rhamnoSCHEMBL765367CHEMBL1535112SCHEMBL30595473

Database identifiers

CAS
520-26-3
PubChem CID
3594
DTXSID
DTXSID50859444
ChEMBL
CHEMBL1535112

Properties

Computed structural properties

XLogP
-1.1
Topological polar surface area
234 Ų
Hydrogen bond donors
8
Hydrogen bond acceptors
15
Rotatable bonds
7
Heavy atoms
43

Physicochemical properties

Melting point
250 · 250-255 °C (dec.)(lit.)
alpha
-76 · -76 º (c=2,pyridine)
Boiling point
576.16 °C · 576.16°C (rough estimate)
Density
1.329 · 1.3290 (rough estimate)
refractive index
1.594 · 1.5940 (estimate)
storage temp.
2 · Sealed in dry,2-8°C

Safety & regulation

Safety data

F
3-10
wgk
3
tsca
TSCA listed
rtecs
MK6650000
hs_code
29389090
risk_code
22-36/37/38

Chemistry & industry

Applications · 9 items

UsesThe product is a vitamin P type medicine. It is mainly used to enhance the toughness of capillaries. The derivative of hesperidin, methyl hesperidin is also vitamin P type medicine. It has been listed in as a variety in Japan's《Japanese Standard of food additives》. It is a vitamin drug which can reduce the fragility of capillary used for the adjuvant treatment of hypertension.

DescriptionHesperidin 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.

DescriptionHesperidin is a flavanone rutinoside first isolated from citrus peels. It is metabolized by intestinal bacteria to an aglycone form, hesperetin (Item No. 10006084), which is thought to be more bioavailable due to reduced polarity that allows for increased cell permeability. At 100 μM, hesperidin has been shown to increase the cytotoxicity of doxorubicin on MCF-7 and HeLa cancer cells in vitro by inhibiting cell cycle progression and upregulating apoptosis. It also is reported to produce estrogenic effects, decreasing serum and hepatic lipid concentrations and reducing osteoporosis in ovariectomized rats. Hesperidin produces free radical scavenging activity in various in vitro antioxidant assays.

HistoryHesperidin 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.

Usesvitamin P is considered a vascular protector and an anti-inflammatory agent, vitamin P is said to promote capillary health and increase resistance to collagen destruction. Vitamin P is a bioflavonoid that can work in conjunction with vitamin C, helping prevent oxidation of the latter. Vitamin P is found in such food sources as apricots, broccoli, citrus fruit pulp, grapes, prunes, and spinach.

UsesHesperidin is a flavoring agent that is a bioflavonoid found in citrus pulp. it has minor use as a flavorant.

UsesA flavanone found in citrus fruits, also regarded as Vitamin P.

Usesantiinflammatory, capillary protectant, hypolipidemic

UsesAnticancer

Suppliers101 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

1 records

Compound notes

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