3D Mol Similar

Apigenin

: Iupac Name：5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one; CAS No.: 520-36-5; Molecular Weight：270.24; Modify Date.: 2022-10-31 23:05; Introduction: Apigenin (chemically known as 4′, 5, 7-trihydroxyflavone, with molecular formula C15H10O5) is with molecular weight of 270.24. It is a naturally occurring plant flavone and is abundantly present in common fruits such as grapefruit, plant-derived beverages, and vegetables such as parsley, onions, oranges, tea, chamomile, wheat sprouts and in some seasonings.Apigenin has gained particular interest in recent years as a beneficial and health promoting agent owing to its low intrinsic toxicity and its striking effects on normal versus cancer cells, compared with other structurally-related flavonoids. It has been increasingly recognized as a cancer and tumor chemopreventive agent (for breast cancer, cervical cancer, colon cancer, hematologic cancer, lung cancer, ovaria cancer, prostate cancer, skin cancer, thyroid cancer, endometrial cancer, gastric cancer, liver cancer, adrenal cortical cancer, leukemia, and neuroblastoma) owing to its anti-inflammatory, antioxidant and anticancer properties. View more+

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1. Names and Identifiers

: 1.1 Name; Apigenin; 1.2 Synonyms; 4',5,7-Trihydroxyflavone 4,5,7-Trihydroxyflavone (apigenin) 4’,5,7-trihydroxyflavaone 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)- 5,7,4'-trihydroxyflavone 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one APIGENIN CRYSTALLINE APIGENIN FROM PARSLEY Apigenine apigenol C.I. NATURAL YELLOW 1 Celery seed extract CHAMOMILE EINECS 208-292-3 Matricaria chamomilla flower MFCD00006831 Pelargidenon 1449 Pelargidenone T66 BO EVJ CR DQ& GQ IQ Versulin Versuline; View all

1.3 CAS No.: 520-36-5

1.4 CID: 5280443

1.5 EINECS(EC#): 208-292-3

1.6 Molecular Formula: C15H10O5 (isomer)

1.7 Inchi: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H

1.8 InChIkey: KZNIFHPLKGYRTM-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O

1.10 Isomers Smiles: C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O

2. Properties

2.1 Density: 1.548

2.1 Melting point: 345-350℃

2.1 Boiling point: 555.5 °C at 760 mmHg

2.1 Refractive index: 1.732

2.1 Flash Point: 217 °C

2.1 Precise Quality: 270.05300

2.1 PSA: 90.90000

2.1 logP: 2.57680

2.1 Solubility: DMSO: 27?mg/mL

2.2 Appearance: Pale Yellow Crystalline Solid

2.3 Storage: Keep Cold.

2.4 Color/Form: yellow

2.5 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.6 Physical: Solid

2.7 pKa: 6.53±0.40(Predicted)

2.8 Water Solubility: DMSO: 27?mg/mL

2.9 Spectral Properties: UV max (ethanol): 269, 340 nm (epsilon 18,800; 20,900)
MASS: 98432 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
UV: 6-580 (Phillip et al., Organic Electronic Spectral Data, John Wiley & Sons, New York)

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 56 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 22 of 56 companies. For more detailed information, please visit ECHA C&L website

Of the 6 notification(s) provided by 34 of 56 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (97.06%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501; View all

3.2 Methods of Manufacturing: The aglucon of apiin; and of apigenin-7-glucoside;. From apiin; by boiling with acids, from apigenin-7-glucoside; by enzymatic hydrolysis with emulsion or by boiling with 15% H2SO4

3.3 Purification Methods: Crystallise it from aqueous pyridine or aqueous EtOH. It dyes wool yellow when mixed with Cr ions. [Beilstein 18 H 181, 18 I 396, 18 II 178, 18 III/IV 2682, 18/4 V 574.] ApigeninSupplier

3.4 Usage: antispasmodic, antineoplastic, topoisomerase I inhibitor

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S36

4.1 Octanol/Water Partition Coefficient: log Kow = 3.02

4.2 Hazard Declaration: H315-H319-H335

4.2 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.3 RIDADR: OTH

4.3 Caution Statement: P261-P305 + P351 + P338

4.3 WGK Germany: 3

4.3 RTECS: LK9276000

4.3 Safety: Mutation data reported. A mild allergen. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
Hazard Codes?of Apigenin (CAS NO.520-36-5):?Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36: Wear suitable protective clothing.
WGK Germany: 3
RTECS: LK9276000
F: 10

4.4 Specification: ? Apigenin , with CAS number of 520-36-5, can be called Apigenin, 98% (HPLC) ; 2-(p-Hydroxyphenyl)-5,7-dihydroxychromone ; Flavone, 4,5,7-trihydroxy- ; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone ; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)- (9CI) ; 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one ; 4H-1-Benzopyran-4-one,5,7-dihydroxy-2- (4-hydroxyphenyl)- . Apigenin (CAS NO.520-36-5) is a potent inhibitor of CYP2C9, an enzyme responsible for the metabolism of many pharmaceutical drugs in the body. Apigenin is a flavone that is the aglycone of several glycosides. Apigenin is a yellow crystalline solid that has been used to dye wool.

4.5 Toxicity

1.	???	mmo-sat 100?μg/plate	???	BCSTB5 ?? Biochemical Society Transactions. 5 (1977),1489.
2.	???	mma-sat 100?μg/plate	???	BCSTB5 ?? Biochemical Society Transactions. 5 (1977),1489.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

520-36-5Total: 52 Synthesis Route

90-24-4 37 Suppliers

520-36-5 373 Suppliers

Literatures:
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, , vol. 19, # 7 p. 583 - 586
Yield: null

99-76-3 528 Suppliers

520-36-5 373 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 56, # 16 p. 4884 - 4887
Yield: null

480-41-1 187 Suppliers

520-36-5 373 Suppliers

Literatures:
Bovicelli, Paolo; D'Angelo, Vittoria; Collalto, Daniela; Verzina, Antonio; D'Antona, Nicola; Lambusta, Daniela Journal of Pharmacy and Pharmacology, 2007 , vol. 59, # 12 p. 1697 - 1701
Yield: ~95%

View all

7. Precursor and Product

precursor:

90-24-4

578-74-5

64325-11-7

94805-88-6

99-76-3

5128-44-9

76288-41-0

29741-09-1

123-11-5

5631-70-9

28757-27-9

83171-42-0

480-66-0

480-40-0

100-07-2

480-41-1

35095-48-8

3420-72-2

480-44-4

108-73-6

20486-34-4

View all

product :

76288-50-1

5128-44-9

29741-09-1

5689-38-3

76288-42-1

70872-32-1

76288-44-3

76288-54-5

491-70-3

3316-46-9

1019-52-9

68097-13-2

76288-47-6

437-64-9

480-41-1

529-53-3

76288-49-8

68097-12-1

1151-98-0

3420-72-2

480-44-4

96333-59-4

4323-80-2

View all

8. Other Information

8.0 Chemical Properties: Apigenin (C15H10O5, CAS registry No. 520-36-5) is also called 4’,5,7-trihydroxyflavone, which is a pale yellow crystalline solid. Its melting point is 345-350 oC, and flash point is 217 oC. The solubility of apigenin is 27 g/L in DMSO. Apigenin has a very low solubility in water (1.35 μg/mL) and high permeability. Taking into consideration its high permeability, apigenin is categorized as a Class II drug according to Biopharmaceutics Classification System (BCS), whose characteristics are low solubility and high permeability. Pure apigenin is generally regarded as unstable for long term storage at room temperature, and thus it requires storage at -20°C..

8.1 Occurance: Apigenin is one of the most widespread flavonoids in plants and formally belongs to the flavone sub-class. Of all the flavonoids, apigenin is one of the most widely distributed in the plant kingdom, and one of the most studied phenolics. Apigenin is present principally as glycosylated in significant amount in vegetables (parsley, celery, onions) fruits (oranges), herbs (chamomile, thyme, oregano, basil), and plant-based beverages (tea, beer, and wine). Plants belonging to the Asteraceae, such as those belonging to Artemisia, Achillea, Matricaria, and Tanacetum genera, are the main sources of this compound. However, species belonging to other families, such as the Lamiaceae, for instance, Sideritis and Teucrium, or species from the Fabaceae, such as Genista, showed the presence of apigenin in the aglycone form and/or its C- and O-glucosides, glucuronides, O-methyl ethers, and acetylated derivatives.

8.2 Preparation: Biogenetically, apigenin is a product of the phenylpropanoid pathway and may be obtained from both phenylalanine and tyrosine, two shikimate-derived precursors. From phenylalanine, cinnamic acid is formed by non-oxidative deamination and then by oxidation at C-4, which is then converted to p-coumaric acid, whereas from tyrosine p-coumaric acid is formed directly by deamination. After activation with CoA, p-coumarate is condensed with three malonyl-CoA residues and then subjected to aromatization by chalcone synthase to form chalcone, which is further isomerized by chalcone isomerase to form naringenin; finally, a flavanone synthase oxidizes naringenin to apigenin.

8.3 Health Benifits: A high number of studies carried out over the years have indicated that apigenin has many interesting pharmacological activities and nutraceutical potential. As an example, its properties as an antioxidant are well known, and it can also be a therapeutic agent to overcome diseases like inflammation, autoimmune, neurodegenerative disease, and even several types of cancers. It has a low intrinsic toxicity on normal versus cancerous cells, compared with other structurally related flavonoids.

8.4 Occurrence: Chamomile is a perennial found in Europe.

8.5 Biochem/physiol Actions: A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53. Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication.

8.6 Usage: 4',5,7-Trihydroxyflavone is a nonmutagenic flavonoid shown to inhibit cell proliferation, angiogenesis and protein kinase. Also induces apoptosis in breast cancer cells. It inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication.

8.7 Merck: 14,730

8.8 BRN: 262620

8.9 References: [1] Sanjeev Shukla, Sanjay Gupta (2010) Apigenin: a promising molecule for cancer prevention, 27, 962-978.
[2] https://en.wikipedia.org/wiki/Apigenin
[3] http://bodynutrition.org/apigenin/

8.10 Chemical Properties: Pale Yellow Crystalline Solid

8.11 Uses: antispasmodic, antineoplastic, topoisomerase I inhibitor

8.12 Uses: Induces the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentration (12.5 uM) by inhibiting MAP kinase activity. Also inhibits the proliferation of malignant tum or cells by G2/M arrest and induces morphological differentiation. Apigenin has also been reported to enhance the gap juntion intracellular communication in liver cells.

8.13 Uses: Has been used to dye Cr mordanted wool yellow. The color is fast to soap.

8.14 General Description: The herb known as chamomile is derived from the plants Matricaria chamomilla (German, Hungarian, or genuine chamomile) and Anthemis nobilis (English, Roman, or common chamomile). Plants from the two genera have similar activities. The medicinal components are obtained from the flowering tops. The flowers are dried and used for chamomile teas and extracts. Chamomile has been used medicinally for at least 2,000 years. The Romans used the herb for its medicinal properties, which they knew were antispasmodic and sedative.
The herb also has a long history in the treatment of digestive and rheumatic disorders. The activity of chamomile is found in a light blue essential oil that composes only 0.5% of the flower. The blue color is caused by chamazulene, 7-ethyl-1,4-dimethylazulene . This compound is actually a byproduct of processing the herb. The major component of the oil is the sesquiterpene (-)-α-bisabolol. Also present are apigenin, angelic acid, tiglic acid, the terpene precursors (farnesol, nerolidol, and germacranolide) coumarin, scopoletin-7-glucoside, umbelliferone, and herniarin. Much of the effect of chamomile is caused by bisabolol . Bisabolol is a highly active anti-inflammatory agent in various rodent inflammation and arthritis tests.; View all

8.15 Biological Activity: Protein kinase inhibitor. Suppresses tumor-promoting effects of TPA and exhibits antiproliferative activity in human breast cancer cells (IC 50 values are 59.44 and 31.15 μ M at 24 and 72 hrs respectively). Activates both the intrinsic and extrinsic apoptotic pathways and displays anti-inflammatory, hypotensive, antispasmodic and antioxidant properties in vivo .

8.16 Anticancer Research: It is a flavone compound found in many fruits and vegetables and abundant in chamomiletea, parsley, celeriac, and celery. It induces apoptosis by targeting leptin/leptin receptor pathway and by targeting caspase-dependent extrinsic pathway aswell as STAT3 signaling pathway in lung adenocarcinoma and BT-474 breast cancercells, respectively (Singh et al. 2016b). It shows antitumor activity against breastcancer MCF-7 cells and colon cancer HCT 116 cells and is a mediator of cancerchemoprevention and an inducer of autophagy. It can be used to treat colon canceras it induces apoptosis in colon cancer cells. It also increase melanogenesis in B16cells by activating the p38 MAPK pathway (Wang et al. 2012).

8.17 Purification Methods: Crystallise it from aqueous pyridine or aqueous EtOH. It dyes wool yellow when mixed with Cr ions. [Beilstein 18 H 181, 18 I 396, 18 II 178, 18 III/IV 2682, 18/4 V 574.]

9. Computational chemical data

Molecular Weight: 270.24g/mol
Molecular Formula: C₁₅H₁₀O₅
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 270.05282342
Monoisotopic Mass: 270.05282342
Complexity: 411
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 87
Heavy Atom Count: 20
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwYIAAAAAAAACBQAAAGgAACAAADASAmAAwBoAABgCIAqBSAAACCAAkIAAIiAEGCMgMJzaGNRqCeWCl4BUIuQeI7KzOIAAACAAIAABAAAAQABAAAAAAAAAAAA==

10. Question & Answer

What Are the Potential Health Benefits of Apigenin? May 30 2023
General Description Apigenin, a naturally occurring flavone belonging to the class of compounds called flavonoids, offers numerous health benefits. Found in plants such as parsley, chamomile, and cele..
What are the plant sources of Apigenin? Feb 20 2023
Apigenin is widely distributed in nature and belongs to a class of flavonoid compounds. It can be found not only in some plants but also in common fruits and vegetables. So, what are the plant sources..
What is Apigenin and How Can It Benefit Your Health? Feb 12 2023
Apigenin, also known as 4',5,7-trihydroxyflavone (4',5,7-THF), is a natural flavonoid compound found in various plants. Properties and Presence Apigenin belongs to the flavonoid group and is abundantl..
What are the pharmacological effects of Apigenin? Aug 01 2022
Apigenin, also known as luteolin, is a flavonoid compound that is widely distributed in nature, mainly found in plants and fruits, with celery being relatively high in content. Most experiments have s..

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