[ CAS No. 578-74-5 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 578-74-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 578-74-5 ]

SDS Specification

Alternatived Products of [ 578-74-5 ]

Product Details of [ 578-74-5 ]

CAS No. :	578-74-5	MDL No. :	MFCD00016787
Formula :	C₂₁H₂₀O₁₀	Boiling Point :	-
Linear Structure Formula :	C₁₅H₉O₅(C₆H₁₁O₅)	InChI Key :	KMOUJOKENFFTPU-QNDFHXLGSA-N
M.W :	432.38	Pubchem ID :	5280704
Synonyms :	Apigetrin;Cosmosiin;NSC 407303;Apigenin-7-O-β-D-glucoside;7-O-β-D-Glucopyranosylapigenin;Cosmosin;Thalictiin;Cosmosioside;Cosmetin;Apigenin 7-glucoside	Chemical Name :	5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

Safety of [ 578-74-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 578-74-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 578-74-5 ]

[ 578-74-5 ] Synthesis Path-Upstream 1~14

1
[ 119249-30-8 ]
[ 578-74-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With water; ammonium hydroxide In methanol at 20℃; for 12 h;	Compound 1 (150 mg, 0.25 mmol) was added to a solution of 30percent aq NH₃*H₂O (5 mL) in CH₃OH (20 mL) with stirring. After stirring for 12 h at room temperature, the solvent was removed under reduced pressure. The residual was chromatographed on silica gel using ethyl acetate/MeOH (3:1) as eluent to afford the yellow solid 78 mg, yield: 72percent. Mp 234-236 °C. (lit. 13, 238-239 °C); IR (KBr, cm^-1) 3440, 2918, 1615, 1563, 1452, 1346, 1273, 1245, 1146, 1103, 1072, 1024, 895; ¹H NMR (400 MHz, DMSO-d₆) δ 12.97 (s, 1H, OH-5), 10.48 (s, 1H, OH-4'), 7.96 (d, J = 8.8 Hz, 2H, H-2', H-6'), 6.94 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.87 (s, 1H, H-3), 6.83 (d, J = 1.6 Hz, 1H, H-8), 6.45 (d, J = 1.6 Hz, 1H, H-6), 5.42 (d, J = 8.0 Hz, 1H, H-1), 5.15 (s, 1H, OH-2), 5.08 (s, 1H, OH-3), 5.06 (s, 1H, OH-4), 4.63 (s, 1H, OH-6), 3.72-3.70 (m, 1H, H-2), 3.49-3.18 (m, 5H, H-3,4,5, 6); ¹³C NMR (100 MHz, DMSO-d₆) δ 60.6, 69.6, 73.1, 76.5, 77.2, 94.8, 99.6, 99.9, 103.1, 105.4, 116.0, 121.1, 128.6, 156.9, 161.1, 161.4, 163.0, 164.3, 180.1; HRMS [M+Na]⁺ calcd for C₂₁H₂₀O₁₀Na 455.3665, found 455.3649.

Reference： [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034
[2] Carbohydrate Research, 2012, vol. 357, p. 41 - 46

2
[ 1145669-48-2 ]
[ 578-74-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium methylate In methanol; dichloromethane at 20℃;	Compound 9a (104 mg, 0.1 mmol) was dissolved in CH₂Cl₂ (2 mL) and anhydrous methanol (3 mL) was added. Sodium methoxide (100 mg, 1.85 mmol) was then added and the reaction was stirred at room temperature and monitored by TLC. Upon completion, the reaction was neutralized by adding freshly prepared 1 M HCl/MeOH solution to a pH value of 7.4. The solution was then concentrated under reduced pressure to give a yellow oil (crude product), which was further purified by preparative TLC plate to afford glycoside 9b as a white solid, 33 mg, 77percent. ¹H NMR (400 MHz, DMSO-d₆) δ 7.95 (d, J = 8.8 Hz, 2H), 6.97 (d, J = 8.8 Hz, 2H), 6.86 (s, 1H), 6.84 (d, J = 1.4 Hz, 1H), 6.44 (d, J = 1.8 Hz, 1H), 5.07 (d, J = 7.5 Hz, 1H), 3.71 (d, J = 10.7 Hz, 1H), 3.47 – 3.21 (m, 5H); ¹³C NMR (100 MHz, DMSO-d₆) δ 182.45 (C-4), 164.81 (C-7), 163.41 (C-2), 162.29 (C-5), 161.58 (C-9), 157.41 (C-4'), 129.05 (C-2',6'), 121.15 (C-1'), 116.58 (C-3',5'), 105.79 (C-10), 103.42 (C-3), 100.34 (Glc-C-1), 99.98 (C-6), 95.29 (C-8), 77.63 (Glc-C-3), 76.91 (Glc-C-5), 73.58 (Glc-C-2), 69.99 (Glc-C-4), 61.02 (Glc-C-6).

Reference： [1] Tetrahedron Letters, 2018, vol. 59, # 50, p. 4442 - 4447

3
[ 17306-46-6 ]
[ 520-36-5 ]
[ 578-74-5 ]

Yield	Reaction Conditions	Operation in experiment
3.4 g	Stage #1: With aluminium(III) chloride hexahydrate In methanol at 70℃; for 15 h; Sealed tube Stage #2: With phosphoric acid In methanol for 0.5 h; Sonication	5.0 g of 6H2O-aluminum trichloride, 100 ml of methanol,98percent wild luteolin 10g,70 sealed hydrolysis 15h, Adding phosphoric acid 6ml,Mixing,Ultrasound 30min,Adding 0.1percent phosphoric acid in 1000ml of the solution with stirring slowly, placing the mixture for 30 minutes, placing overnight, filtering and washing the filter cake to obtain a mixture of wild erosin, apigenin-7-O-glucoside and apigenin; The column was eluted with chloroform-methanol (12: 1), then apigenin was first eluted, and the ratio of chloroform to methanol was adjusted to (6: 1) to give apigenin-7-O- Glucoside 3.4g, determined by HPLC content of 98.3percent, and finally out of a small amount of wild lacquer glycosides

Reference： [1] Patent: CN105481916, 2016, A, . Location in patent: Paragraph 0018

4
[ 133-89-1 ]
[ 2196-14-7 ]
[ 578-74-5 ]

Reference： [1] Nature Communications, 2017, vol. 8, # 1,

5
[ 31087-58-8 ]
[ 578-74-5 ]

Reference： [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034

6
[ 480-41-1 ]
[ 578-74-5 ]

Reference： [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034

7
[ 572-09-8 ]
[ 578-74-5 ]

Reference： [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034

8
[ 23598-19-8 ]
[ 578-74-5 ]

Reference： [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46

9
[ 52309-82-7 ]
[ 578-74-5 ]

Reference： [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46

10
[ 10236-47-2 ]
[ 578-74-5 ]

Reference： [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46

11
[ 26544-34-3 ]
[ 2280-44-6 ]
[ 30738-01-3 ]
[ 139759-42-5 ]
[ 578-74-5 ]

Reference： [1] Liebigs Annalen der Chemie, 1992, # 6, p. 575 - 580

12
[ 26544-34-3 ]
[ 2280-44-6 ]
[ 520-36-5 ]
[ 139759-42-5 ]
[ 578-74-5 ]

Reference： [1] Liebigs Annalen der Chemie, 1992, # 6, p. 575 - 580

13
[ 123656-62-2 ]
[ 107-93-7 ]
[ 578-74-5 ]

Reference： [1] Chemistry of Natural Compounds, 1989, vol. 25, p. 303 - 308[2] Khimiya Prirodnykh Soedinenii, 1989, # 3, p. 352 - 359

14
[ 520-36-5 ]
[ 572-09-8 ]
[ 578-74-5 ]

Reference： [1] Yakugaku Zasshi, 1940, vol. 60, p. 502,505; engl. Ref. S. 190[2] Chem.Abstr., 1941, p. 4022

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Technical Information

? Appel Reaction ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chugaev Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Nomenclature of Ethers ? Oxidation of Alcohols by DMSO ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Ethers ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Ethers ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Ritter Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 578-74-5 ]

Aryls

[ 520-27-4 ]

5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

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1-(4-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one

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Ethers

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(S)-5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one

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2-(3,4-Bis(2-hydroxyethoxy)phenyl)-5-hydroxy-7-(2-hydroxyethoxy)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

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H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 578-74-5 ] {[proInfo.proName]}

Quality Control of [ 578-74-5 ]

Related Doc. of [ 578-74-5 ]

Product Details of [ 578-74-5 ]

Safety of [ 578-74-5 ]

Application In Synthesis of [ 578-74-5 ]

[ 578-74-5 ] Synthesis Path-Upstream 1~14

Technical Information

Related Functional Groups of [ 578-74-5 ]

Aryls

Ethers

Alcohols

Ketones

Related Parent Nucleus of [ 578-74-5 ]

Other Aromatic Heterocycles

Tetrahydropyrans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 578-74-5 ]

Related Parent Nucleus of
[ 578-74-5 ]