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Best price magnolia bark extract 98% honokiol powder
Cas No: 35354-74-6
USD $ 2.0-3.0 / Kilogram 1 Kilogram 10 Metric Ton/Month Shaanxi Greenyo Biotech Co., Ltd. Contact Supplier
magnolia bark extract honokiol 98%
Cas No: 35354-74-6
USD $ 243.0-243.0 / Kilogram 1 Kilogram 1 Metric Ton/Month Changsha Staherb Natural Ingredients Co.,Ltd Contact Supplier
Antibacterial standardized herbal extract Honokiol CAS:35354-74-6
Cas No: 35354-74-6
USD $ 92.0-96.0 / Kilogram 1 Kilogram 10000 Kilogram/Month Baoji Guokang Healthchem co.,ltd Contact Supplier
Supply Magnolia Bark Extract Honokiol 98% 35354-74-6
Cas No: 35354-74-6
No Data 1 Kilogram 1 Metric Ton/Month Nanjing Manhay Medical Technology Co.,Ltd Contact Supplier
Honokiol Manufacturer/High quality/Best price/In stock
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USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality Honokiol supplier in China
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No Data 1 Metric Ton 30 Metric Ton/Month Simagchem Corporation Contact Supplier
Honokiol Cistanche Extract with best price and top quality
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USD $ 800.0-1000.0 / Kilogram 1 Kilogram 5000 Kilogram/Month Kono Chem Co.,Ltd Contact Supplier
High Content Natural Extract Honokiol HACCP manufacturer
Cas No: 35354-74-6
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
Factory Supply Honokiol
Cas No: 35354-74-6
No Data 1 1 Ality Chemical Corporation Contact Supplier
4-phenyl-6,6-bis(prop-2-enyl)cyclohexa-1,3-diene-1,3-diol
Cas No: 35354-74-6
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier

35354-74-6 Usage

Basic Information

Honokiol is the isomer of magnolol, being the dimer polymerized by the side chain of phenylpropane and another phenylpropyl benzene nucleus, called the neolignan. It was mainly found in the Lauraceae plants, being the active ingredients of antibacterial, anti-inflammatory of the traditional Chinese medicine Magnolia. Honokiol and magnolol appear as colorless needle crystal, being insoluble in water, soluble in chloroform, benzene, ethanol and caustic alkali. The physical and chemical constants were honokiol, mp: 102 ° C, UV λmaxEtOHnm (ε): 294 (8200); and honokiol, mp: 87.5 ° C, UV λmaxEtOHnm (ε): 294 nm (8200). Figure 1 shows the chemical formula of magnolol and honokiol. Magnolia is a commonly used Chinese medicine. First contained in the "Shen Nong's Herbal Classic", as the goods. Magnolia officinalis extract is a product derived from dried root bark, bark or shoots of Magnolia officinalis, etc. The product extracts usually standardize the contents of magnolol and honokiol.

Distribution

There were about 90 species of Magnoliaceae Magnolia plants around the world. There are about 30 species, of which there are about 20 kinds of medicinal value. Magnolia was born at fertile-soil, soil-deep sunny hillside, forest edge of an altitude of 300~1700 m. Magnolia is mainly distributed in western Hubei, southern Sichuan, southern Shaanxi and southern Gansu. Magnolia is mainly distributed in Jiangxi, Anhui, Zhejiang, Fujian, Hunan, Guangxi and northern Guangdong. Magnolia officinalis has a large area of artificial cultivation.

Main Ingredients

Magnolia bark contains magnolol, and honokiol, isomagnolol and other ingredients. It has been isolated of the trihydroxy honokiol, degausated trihydroxy glibenol, trihydroxy thick aldehydes, poly honokiol a, c. from the ethyl acetate extract of magnolia. Bark contains about 1% volatile oil, which mainly contains β-oleyl alcohol; still contain α-pinene, β-pinene and limonene. The bark also contains lignin. Its leaves also contain magnolol and honokiol. [Harvest and Processing] On April to June, pick off the dried bark growing for more than 15 years, and put into the boiling water for micro-cook, and put into the soil pits, covered with grass to "sweat". When the water comes from the internal seepage and the inner surface becomes purple brown or tan, further steamed soft, remove out, roll into tube-like, and dry it Root bark and branch, after being peel down, can be directly dried. Figure 2 is Magnolia.

Extraction method

1. Magnolia extract (flow extract) production process Take magnolia and crush it, infiltrate with ethanol for 12 hours, and place it into the percolation tube; apply 12 times the amount of ethanol for percolation; collect the percolation fluid; decompress and completely recycle the ethanol to obtain the flow extract with a yield of about 9% and the content of solid content being 85.0%. The product contains more than 11.0% of magnolol and over 5.0% honokiol. 2. Magnolol, and Honokiol extraction and separation Take the thick and dry powder of magnolia officinalis, add 1/5 amount (W / W) of lime powder, mix well; apply 15-20 times the amount of distilled water for percolation; the percolation fluid plus hydrochloric acid was adjusted to the pH value of 2 to 3, Stand still. The precipitate was collected and washed with distilled water until the pH of the precipitate was 6 to 7. After drying, alumina (1: 10) was added and homogenized, and the extractant was extracted with cyclohexane. The cyclohexane was concentrated and allowed to cool to precipitate out the white crystals; filter to give crystals and mother liquor. Crystal is recrystallized from cyclohexane, i.e., honokiol. The mother liquor is concentrated to crystallize, further re-crystallized by cyclohexane to give colorless flaky crystals, which are magnolol crystals. The yield of honokiol was 85%, and the yield of honokiol was 74%.

Pharmacological effects

1. The role of anti-pathogenic microorganisms Magnolia has inhibitory effect against Staphylococcus aureus, Streptococcus cholerae, Escherichia coli, Proteus, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Proteus Bacilli subtilis, diphtheria bacillus and other Gram-negative bacteria, of which it has the strongest inhibitory effect on Staphylococcus aureus. At the concentration of 15%, it has inhibitory effect against the skin fungi of experimental animals including small spore ringworm, genital trichophyton and Trichophyton rubrum. Magnolia decoctum has some effect on the improvement of parenchymal pathological damage in mice with experimental viral hepatitis. Magnolol had significant antibacterial activity against Gram-positive bacteria and acid-resistant bacteria. Magnolol had significant anti-caries effect and had a minimum inhibitory concentration of 6.3 μg / ml, and its antibacterial activity was stronger than that of typical antimicrobial alkaloids Berberine (MIC: 50 μg / ml). The saturated aqueous solution of the volatile oil of magnesium and Magnolia officinalis has certain antibacterial effect against Staphylococcus aureus, sarcina and Bacillus subtilis. 2. The role of the cardiovascular system Magnolol and honokiol inhibit the formation of thromboxane B2 in various cases, and the increase in intracellular Ca2 + caused by arachidonic acid or collagen is also inhibited by both of them. Honokiol can inhibit CaM to stimulate the activity of the cyclic nucleotide phosphodiesterase. Honokiol, in the presence of Ca2 +, can bind to CaM, thereby antagonizing its activation of phosphodiesterase. In addition, honokiol has a stimulating effect on the basal activity of CaM-dependent phosphodiesterase. 3. Antitumor effect Magnolol and its hydroxymethyl derivatives have a significant inhibitory effect against the second stage of mice skin tumors. The three extraction components of Magnolia officinalis, lignans, magnolol, and honokiol and monoterpene magnolol are the antagonist of the Epstein -Barr virus early antigen activation effect induced by the 12-O-tetradecanoyl phorbol-13-acetate (TPA). The methanol extract of Magnolia officinalis and magnolol has significant inhibitory effect on the mouse skin tumors induced by the two-stage in vivo carcinogenicity. The toxicity of Magnolia officinalis is relatively small. Magnolia decoction: LD50 of mice subjecting to intraperitoneal injection was 6.12 ± 0.038g / kg; the LD50 for lambda alkaloids subjecting to intraperitoneal injection was 45.55mg / kg. The MLD for cat subjecting to intravenous infusion was 4.25 ± 1.25g / kg. Under the general muscle relaxation dose, the ECG of the experimental animal is not affected. Large doses can cause respiratory depression and death. Pharmacokinetics 14C isotope tracer studies have shown that magnolol has rapid oral administration for rat; after 15 minutes, the plasma concentration reaches the peak. After oral administration of 1 hour, liver, kidney as well as stomach contains significant radioactive. The same results were obtained in 8 hours after 1 hour, and significant radioactivity was observed in the intestine. Magnolol, after subjecting intravenous infusion, is distributed in the brain, spinal cord, liver, stomach, intestine, kidney, lung, heart, muscle and other tissues. Intravenous administration can cause significant blacking in lungs after 1 hour. This is due to that the micro-particles of the magnolol suspension are caught in the lungs. Magnolol is mainly distributed in the liver with remarkable blacking also being found in the intestine. In other tissues, the radioactivity is basically uniform distributed. In the brain, it is also seen of a similar general distribution as muscle. 8 hours later, liver, lung and kidney still contain a number of radioactivities. Remarkable blacking could be seen in the intestine, and so for stomach. Based on the analysis of mass spectrometry, the main metabolites of Magnolol, which excreted in the fecal matter for the rats is M1, M2, M3, M4, M5, M6 and their glucuronic acid compounds and sulfates.

Clinical efficacy

Magnolia can be used to treat acute enteritis, bacterial or amoebic dysentery and chronic gastritis.

Application overview

Magnolia is a kind of traditional Chinese medicine, and has been included in many kinds of prescriptions. In recent years, domestic and foreign scholars, through the in-depth study of the active ingredients, pharmacodynamics and clinical pharmacy of Magnolia officinalis, have developed the Magnolia caries toothpaste, antibacterial “chewing gum” made of Magnolia extract that have been already marketed.

Description

Magnolol is derived from the root bark and branch bark of magnolia or Magnolia officinalis. Magnolia officinalis was first written in the《ben jing》, it prefers cool and humid climate and well-drained acid soil. Cortex magnoliae officinalis (hou po) is mainly produced in Sichuan (Wan quan, Shizhu, Guanxian), Hubei (Shien,Yichang, Lichuan), Zhejiang (Longquan, Anhui), and other places. It is also distributed in Fujian, Jiangxi, Hunan, Guangxi, Yunnan, Guizhou, Shanxi, Gansu, and other places. Cortex magnoliae officinalis from Sichuan and Hubei is called “chuan pu,” with better quality, while in Zhejiang, it is called “warm park,” with a larger output.

Physical properties

Appearance: white fine powder. Solubility: practically insoluble in water; very soluble in benzene, ethyl ether, chloroform, and acetone. Melting point: magnolol is 102 °C. Honokiol is 87.5 °C.

History

In 1930, magnolol was first isolated from the bark of Cortex magnoliae officinalis in China by Japanese Sugii, and it was also isolated from Cortex magnoliae officinalis in Japan. In 1973, magnolol and its isomers honokiol were isolated from Cortex magnoliae officinalis in China and Japan by Japanese Fujita. The drug research and development of magnolol and honokiol remain in pharmacological activity and preclinical research. Kyung Hee University from Korea declared a preclinical study in 2003, in which allergy, anxiety, angina, and heart failure are indications for honokiol.

Uses

Honokiol has been used:to study its effects on plasmid hSirt3102-399 deacetylation activityas an antioxidant to study its cytoprotective role in human ovarian cancer cells (SKOV-3) and Chinese hamster ovary cells (CHOK1)to explore its effects on oxidative stress and mitochondrial dysfunction via a sirt3-dependent mannerfor intracerebroventricular (ICV) cannulation

Uses

Honokiol is a small-molecule polyphenol isolated from the genus Magnolia. Recent studies show that Honokiol displays antiangiogenic, antiinflammatory, and antitumor properties in preclinical models, w ithout appreciable toxicity. Honokiol has been shown to inhibit the bone metastatic growth of human prostate cancer cells.

Indications

These compounds are recorded in the British Pharmacopoeia (2017) and European Pharmacopoeia (8.7th ed.). They are mainly used as antibacterial and antifungal agents.

General Description

Honokiol exhibits analgesic, antithrombotic, antispasmodic, antidepressant, antimicrobial and neuroprotective effects. It regulates gamma-aminobutyric acid (GABA) A receptors. Honokiol is associated with an increased risk of bleeding. It prevents platelet aggregation, protects myocardium from ischemic damage and inhibits ventricular arrhythmia.

Biochem/physiol Actions

Honokiol is a natural biphenyl neolignan from magnolia extract. It is antiangiogenic, antitumor, and anxiolytic.

Pharmacology

Magnolol and honokiol have the pharmacological effects of prolonging central muscle relaxation, inhibition of the central nervous, anti-inflammatory, antibacterial, antimicrobial, antiulcer, antioxidant, antitumor, hormone regulation, and antidiabetes .
InChI:InChI=1/C18H18O2/c1-3-5-13-7-9-18(20)16(11-13)14-8-10-17(19)15(12-14)6-4-2/h3-4,7-12,19-20H,1-2,5-6H2

35354-74-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (H1309)  Honokiol  >95.0%(GC) 35354-74-6 200mg 350.00CNY Detail
TCI America (H1309)  Honokiol  >95.0%(GC) 35354-74-6 1g 990.00CNY Detail
Sigma-Aldrich (Y0001290)  Honokiol  European Pharmacopoeia (EP) Reference Standard 35354-74-6 Y0001290 1,880.19CNY Detail
Sigma-Aldrich (42612)  Honokiol  analytical standard 35354-74-6 42612-25MG 1,232.01CNY Detail
Sigma (H4914)  Honokiol  ≥98% (HPLC), powder 35354-74-6 H4914-10MG 1,456.65CNY Detail
Sigma (H4914)  Honokiol  ≥98% (HPLC), powder 35354-74-6 H4914-25MG 2,932.02CNY Detail

35354-74-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Honokiol

1.2 Other means of identification

Product number -
Other names 5,3'-DIALLYL-2,4'-DIHYDROXYBIPHENYL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:35354-74-6 SDS

35354-74-6Synthetic route

Dimethylhonokiol
68592-18-7

Dimethylhonokiol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
With aluminum (III) chloride at -5 - 0℃; for 0.333333h;97%
With boron tribromide-dimethyl sulfide complex In 1,2-dichloro-ethane at 65℃; for 15h; Reagent/catalyst; Temperature; Inert atmosphere;95%
Stage #1: Dimethylhonokiol With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #3: With water In tetrahydrofuran
57.8%
3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol
68592-19-8

3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
With boron trichloride - methyl sulfide complex In dichloromethane; 1,2-dichloro-ethane for 18h; Reflux;91%
With boron tribromide In dichloromethane at 20℃; for 0.416667h; Inert atmosphere;90%
With boron tribromide at -15 - 20℃;
With boron tribromide In dichloromethane at 20℃; for 0.416667h; Inert atmosphere;430 mg
5-allyl-4'-(allyloxy)-[1,1'-biphenyl]-2-ol
108886-93-7

5-allyl-4'-(allyloxy)-[1,1'-biphenyl]-2-ol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
With N,N-diethylaniline at 200℃; for 24h; Claisen Rearrangement; Sealed tube; Schlenk technique; Inert atmosphere;90%
With boron trichloride In chlorobenzene at -15℃; for 1h;80%
5,3'-diallyl-2,4'-bis-methoxymethoxy-biphenyl
711012-14-5

5,3'-diallyl-2,4'-bis-methoxymethoxy-biphenyl

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃; for 44h;89%
3,5'-diallyl-2'-(methoxymethoxy)-[1,1'-biphenyl]-4-ol

3,5'-diallyl-2'-(methoxymethoxy)-[1,1'-biphenyl]-4-ol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
With methanol; chloro-trimethyl-silane at 0 - 20℃; for 6h;85%
2,4'-bis-O-allylbiphenyl
911812-86-7

2,4'-bis-O-allylbiphenyl

A

3,3'-diallyl biphenyl-2,4'-diol

3,3'-diallyl biphenyl-2,4'-diol

B

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
for 1.33333h; Claisen Rearrangement; Microwave irradiation; Heating; Sealed tube;A 40%
B 60%
at 180℃; for 1.33333h; Claisen Rearrangement; Microwave irradiation;A 40%
B 60%
at 190℃; for 12h; Claisen Rearrangement; Sealed tube;A 55%
B 40%
at 190℃; for 12h; Claisen Rearrangement; Sealed tube;A 55%
B 40%
5-allyl-4'-(allyloxy)-2-methoxybiphenyl
1133087-04-3

5-allyl-4'-(allyloxy)-2-methoxybiphenyl

A

Honokiol
35354-74-6

Honokiol

B

5-allyl-[1,1'-biphenyl]-2,4'-diol
1253950-18-3

5-allyl-[1,1'-biphenyl]-2,4'-diol

Conditions
ConditionsYield
With boron trichloride - methyl sulfide complex In dichloromethane; 1,2-dichloro-ethane for 18h; Claisen rearrangement; Reflux;A 47%
B 49%
Conditions
ConditionsYield
With trifluoroacetic acid In benzene
Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 10h; Ambient temperature;A 7 mg
B 3 mg
5-bromosalicyclic acid
89-55-4

5-bromosalicyclic acid

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 100 percent / aq. H2SO4 / Heating
2: 100 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
3: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C
4: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
5: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
6: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
7: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
8: 52 percent / CuI / tetrahydrofuran / -26 °C
9: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
methyl 3-bromo-4-hydroxybenzoate
29415-97-2

methyl 3-bromo-4-hydroxybenzoate

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
2: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C
3: 100 percent / imidazole / dimethylformamide / 20 °C
4: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
5: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
6: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
7: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
8: 52 percent / CuI / tetrahydrofuran / -26 °C
9: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
5-bromo-2-hydroxy-benzoic acid methyl ester
4068-76-2

5-bromo-2-hydroxy-benzoic acid methyl ester

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 100 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
2: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C
3: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
4: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
5: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
6: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
7: 52 percent / CuI / tetrahydrofuran / -26 °C
8: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 80 percent / HBF4; N-bromosuccinimide / acetonitrile / -20 - 20 °C
2: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
3: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C
4: 100 percent / imidazole / dimethylformamide / 20 °C
5: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
6: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
7: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
8: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
9: 52 percent / CuI / tetrahydrofuran / -26 °C
10: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
(3-bromo-4-methoxymethoxy-phenyl)-methanol
162269-91-2

(3-bromo-4-methoxymethoxy-phenyl)-methanol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 100 percent / imidazole / dimethylformamide / 20 °C
2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
6: 52 percent / CuI / tetrahydrofuran / -26 °C
7: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
5-bromo-2-methoxymethoxy-benzoic acid methyl ester
711012-12-3

5-bromo-2-methoxymethoxy-benzoic acid methyl ester

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C
2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
6: 52 percent / CuI / tetrahydrofuran / -26 °C
7: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
3-bromo-4-methoxymethoxybenzoic acid methyl ester
672922-57-5

3-bromo-4-methoxymethoxybenzoic acid methyl ester

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C
2: 100 percent / imidazole / dimethylformamide / 20 °C
3: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
4: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
5: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
6: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
7: 52 percent / CuI / tetrahydrofuran / -26 °C
8: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
(3-bromo-4-methoxymethoxy-benzyloxy)-tert-butyl-dimethyl-silane
711012-11-2

(3-bromo-4-methoxymethoxy-benzyloxy)-tert-butyl-dimethyl-silane

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
2: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
3: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
4: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
5: 52 percent / CuI / tetrahydrofuran / -26 °C
6: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

acid

acid

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 99 percent / aq. H2SO4 / Heating
2: 80 percent / HBF4; N-bromosuccinimide / acetonitrile / -20 - 20 °C
3: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
4: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C
5: 100 percent / imidazole / dimethylformamide / 20 °C
6: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
7: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
8: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
9: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
10: 52 percent / CuI / tetrahydrofuran / -26 °C
11: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
2-methoxymethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester
711012-10-1

2-methoxymethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
2: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
3: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
4: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
5: 52 percent / CuI / tetrahydrofuran / -26 °C
6: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
5,3'-bis-bromomethyl-2,4'-bis-methoxymethoxy-biphenyl
711012-16-7

5,3'-bis-bromomethyl-2,4'-bis-methoxymethoxy-biphenyl

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / CuI / tetrahydrofuran / -26 °C
2: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
(3'-hydroxymethyl-6,4'-bis-methoxymethoxy-biphenyl-3-yl)-methanol
711012-13-4

(3'-hydroxymethyl-6,4'-bis-methoxymethoxy-biphenyl-3-yl)-methanol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
2: 52 percent / CuI / tetrahydrofuran / -26 °C
3: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
5'-(tert-butyl-dimethyl-silanyloxymethyl)-4,2'-bis-methoxymethoxy-biphenyl-3-carboxylic acid methyl ester
711012-09-8

5'-(tert-butyl-dimethyl-silanyloxymethyl)-4,2'-bis-methoxymethoxy-biphenyl-3-carboxylic acid methyl ester

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
2: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
3: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
4: 52 percent / CuI / tetrahydrofuran / -26 °C
5: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
[5'-(tert-butyl-dimethyl-silanyloxymethyl)-4,2'-bis-methoxymethoxy-biphenyl-3-yl]-methanol
711012-15-6

[5'-(tert-butyl-dimethyl-silanyloxymethyl)-4,2'-bis-methoxymethoxy-biphenyl-3-yl]-methanol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
2: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
3: 52 percent / CuI / tetrahydrofuran / -26 °C
4: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme
4-(prop-2-enyl)phenol
501-92-8

4-(prop-2-enyl)phenol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 29.2 percent / acetic acid / 0.25 h / Ambient temperature
2: 1.) methyl iodide, Mg / 1.) ether, reflux, 5 h; 2.) ether, -15 deg C, 30 min
3: 80 percent / BCl3 / chlorobenzene / 1 h / -15 °C
View Scheme
1-allyl-4-oxocyclohexa-2,5-dienylethanoate
108886-90-4

1-allyl-4-oxocyclohexa-2,5-dienylethanoate

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) methyl iodide, Mg / 1.) ether, reflux, 5 h; 2.) ether, -15 deg C, 30 min
2: 80 percent / BCl3 / chlorobenzene / 1 h / -15 °C
View Scheme
methylhonokiol
68592-15-4

methylhonokiol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Stage #1: methylhonokiol With boron tribromide In dichloromethane at -78℃;
Stage #2: With water
Grignard reaction;
5-allyl-4'-(allyloxy)-2-methoxybiphenyl
1133087-04-3

5-allyl-4'-(allyloxy)-2-methoxybiphenyl

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
2: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
2: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme
4-allyl-2-bromo-1-methoxybenzene
87688-94-6

4-allyl-2-bromo-1-methoxybenzene

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere
2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling with ice
3.2: 2.08 h / 20 °C / Inert atmosphere
3.3: 18 h / 140 °C / Inert atmosphere
4.1: sodium iodide; zinc / N,N-dimethyl-formamide / 18 h / 140 °C / Inert atmosphere
5.1: potassium carbonate / acetone / 20 °C / Inert atmosphere
6.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
7.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere
2.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling
3.2: 2 h / 20 °C / Inert atmosphere; Cooling
3.3: 18 h / 140 °C / Inert atmosphere
4.1: potassium carbonate / acetone / 20 °C / Inert atmosphere
5.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
6.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme
5'-allyl-2'-methoxy-biphenyl-4-ol
1133087-02-1

5'-allyl-2'-methoxy-biphenyl-4-ol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 20 °C / Inert atmosphere
2: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
3: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 20 °C / Inert atmosphere
2: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
3: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme
3-(3-bromo-4-methoxy-phenyl)-propane-1,2-diol
1355483-89-4

3-(3-bromo-4-methoxy-phenyl)-propane-1,2-diol

Honokiol
35354-74-6

Honokiol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling with ice
2.2: 2.08 h / 20 °C / Inert atmosphere
2.3: 18 h / 140 °C / Inert atmosphere
3.1: sodium iodide; zinc / N,N-dimethyl-formamide / 18 h / 140 °C / Inert atmosphere
4.1: potassium carbonate / acetone / 20 °C / Inert atmosphere
5.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
6.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling
2.2: 2 h / 20 °C / Inert atmosphere; Cooling
2.3: 18 h / 140 °C / Inert atmosphere
3.1: potassium carbonate / acetone / 20 °C / Inert atmosphere
4.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
5.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme
Honokiol
35354-74-6

Honokiol

benzoyl chloride
98-88-4

benzoyl chloride

3',5-diallyl-2,4'-diphenylformyloxybiphenyl

3',5-diallyl-2,4'-diphenylformyloxybiphenyl

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Cooling with ice;98.4%
Honokiol
35354-74-6

Honokiol

allyl bromide
106-95-6

allyl bromide

3',5-diallyl-2,4'-bis(allyloxy)-1,1'-biphenyl

3',5-diallyl-2,4'-bis(allyloxy)-1,1'-biphenyl

Conditions
ConditionsYield
With potassium carbonate In acetone at 56℃; for 12h;97%
formaldehyd
50-00-0

formaldehyd

Honokiol
35354-74-6

Honokiol

ethylamine
75-04-7

ethylamine

C26H32N2O2

C26H32N2O2

Conditions
ConditionsYield
In 1,4-dioxane; toluene at 120℃; for 24h;95.5%
formaldehyd
50-00-0

formaldehyd

hexan-1-amine
111-26-2

hexan-1-amine

Honokiol
35354-74-6

Honokiol

C34H48N2O2

C34H48N2O2

Conditions
ConditionsYield
In 1,4-dioxane; toluene at 110℃; for 43h;95.5%
Honokiol
35354-74-6

Honokiol

acetic anhydride
108-24-7

acetic anhydride

2,4'-diacetoxy-5,3'-di(2-propenyl)biphenyl
35347-50-3

2,4'-diacetoxy-5,3'-di(2-propenyl)biphenyl

Conditions
ConditionsYield
With pyridine95%
With potassium carbonate at 20℃; for 0.5h;56%
With pyridine at 25℃; for 18h;
With sodium hydrogencarbonate In ethyl acetate for 48h;
Honokiol
35354-74-6

Honokiol

Tetrahydrohonokiol
35406-31-6

Tetrahydrohonokiol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol for 5h; Reflux;94%
With sodium tetrahydroborate; nickel dichloride70%
With hydrogen; palladium on activated charcoal
With palladium on activated charcoal; hydrogen
With Lindlar's catalyst; hydrogen In ethanol at 20℃; under 760.051 Torr; for 24h;
formaldehyd
50-00-0

formaldehyd

Honokiol
35354-74-6

Honokiol

aniline
62-53-3

aniline

C34H32N2O2

C34H32N2O2

Conditions
ConditionsYield
In 1,4-dioxane; toluene at 100℃; for 58h;93.6%
formaldehyd
50-00-0

formaldehyd

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Honokiol
35354-74-6

Honokiol

C32H32N2O4

C32H32N2O4

Conditions
ConditionsYield
In 1,4-dioxane; toluene at 100℃; for 52h;90.8%
4-Nitrophthalonitrile
31643-49-9

4-Nitrophthalonitrile

Honokiol
35354-74-6

Honokiol

C34H22N4O2

C34H22N4O2

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 40℃; for 48h; Inert atmosphere;90%
Honokiol
35354-74-6

Honokiol

ethyl bromoacetate
105-36-2

ethyl bromoacetate

diethyl 2,2'-((3',5-diallyl-[1,1'-biphenyl]-2,4'-diyl)bis(oxy))diacetate
1333391-01-7

diethyl 2,2'-((3',5-diallyl-[1,1'-biphenyl]-2,4'-diyl)bis(oxy))diacetate

Conditions
ConditionsYield
Stage #1: Honokiol With potassium carbonate In N,N-dimethyl-formamide at 20 - 25℃; Williamson synthesis;
Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 30℃; for 6h; Williamson synthesis;
89.3%
Honokiol
35354-74-6

Honokiol

4-allyl-2-(2-methyl-benzofuran-5-yl)phenol
1416567-14-0

4-allyl-2-(2-methyl-benzofuran-5-yl)phenol

Conditions
ConditionsYield
With oxygen; sodium acetate; palladium dichloride In N,N-dimethyl acetamide; water at 60℃; under 6080.41 Torr; for 16h; Autoclave;86%
With oxygen; sodium acetate; palladium dichloride In N,N-dimethyl acetamide; water at 60℃; under 6080.41 Torr; for 16h; Autoclave;86%
With oxygen; sodium acetate; palladium dichloride In N,N-dimethyl acetamide; water at 60℃; under 6000.6 Torr; for 16h; Wacker Oxidation;86%
formaldehyd
50-00-0

formaldehyd

Honokiol
35354-74-6

Honokiol

dimethyl amine
124-40-3

dimethyl amine

3',5-diallyl-3,5'-bis((dimethylamino)methyl)-[1,1'-biphenyl]-2,4'-diol

3',5-diallyl-3,5'-bis((dimethylamino)methyl)-[1,1'-biphenyl]-2,4'-diol

Conditions
ConditionsYield
In methanol; water at 20℃; for 16h;86%
Stage #1: formaldehyd; dimethyl amine With hydrogenchloride In methanol; water at 2 - 35℃; for 1h;
Stage #2: Honokiol In methanol; water at 75℃; for 6h;
60%
Honokiol
35354-74-6

Honokiol

methyl iodide
74-88-4

methyl iodide

Dimethylhonokiol
68592-18-7

Dimethylhonokiol

Conditions
ConditionsYield
With potassium carbonate In acetone for 24h; Reflux;84%
With sodium hydride In water; dimethyl sulfoxide at 0℃;38%
Honokiol
35354-74-6

Honokiol

3',5-diallyl-3,5'-dinitroso-1,1'-biphenyl-2,4'-diphenol

3',5-diallyl-3,5'-dinitroso-1,1'-biphenyl-2,4'-diphenol

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water; acetonitrile at 20℃; for 1.5h; Cooling with ice;79%
With hydrogenchloride; sodium nitrite In water; acetonitrile at 20℃; for 1.5h;79.3%
Honokiol
35354-74-6

Honokiol

3-bromo-1-phenyl-1-propenyl bromide
4392-24-9

3-bromo-1-phenyl-1-propenyl bromide

3',5-diallyl-2E,4'E-bis(cinnamyloxy)-1,1'-biphenyl

3',5-diallyl-2E,4'E-bis(cinnamyloxy)-1,1'-biphenyl

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃;78%
Honokiol
35354-74-6

Honokiol

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

4-allyl-2-(2-((methylthio)methyl)-2,3-dihydrobenzofuran-5-yl)phenol

4-allyl-2-(2-((methylthio)methyl)-2,3-dihydrobenzofuran-5-yl)phenol

Conditions
ConditionsYield
With ammonium iodide at 130℃; for 18h; Schlenk technique;76%
formaldehyd
50-00-0

formaldehyd

Honokiol
35354-74-6

Honokiol

dimethyl amine
124-40-3

dimethyl amine

C21H25NO2

C21H25NO2

Conditions
ConditionsYield
Stage #1: formaldehyd; dimethyl amine In water at 55℃; for 0.666667h; Mannich Aminomethylation;
Stage #2: Honokiol In water
76%
Honokiol
35354-74-6

Honokiol

methyl 2-(2-chlorophenyl)-2-diazoacetate
264882-00-0

methyl 2-(2-chlorophenyl)-2-diazoacetate

methyl 2-(2-chlorophenyl)-2-((5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl)oxy)acetate

methyl 2-(2-chlorophenyl)-2-((5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl)oxy)acetate

Conditions
ConditionsYield
With sewage sludge-derived carbon material treated with perchloric acid In 1,2-dichloro-ethane at 70℃; for 24h;72%
Honokiol
35354-74-6

Honokiol

dimethyl sulfate
77-78-1

dimethyl sulfate

Dimethylhonokiol
68592-18-7

Dimethylhonokiol

Conditions
ConditionsYield
With sodium In ethanol for 5h; Inert atmosphere; Reflux;70%
Honokiol
35354-74-6

Honokiol

3,3'-(4,6'-dihydroxy-[1,1'-biphenyl]-3,3'-diyl)bis(propane-1,2-diol)

3,3'-(4,6'-dihydroxy-[1,1'-biphenyl]-3,3'-diyl)bis(propane-1,2-diol)

Conditions
ConditionsYield
Stage #1: Honokiol With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h;
Stage #2: With sodium hydroxide In tetrahydrofuran for 1h; Reflux;
66%
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
2: sodium hydroxide; water / tetrahydrofuran / 1 h / Reflux
View Scheme
Honokiol
35354-74-6

Honokiol

C18H17IO2

C18H17IO2

Conditions
ConditionsYield
With iodine In ethanol; water at 50℃; for 12h;65.87%
formaldehyd
50-00-0

formaldehyd

Honokiol
35354-74-6

Honokiol

3',5-diallyl-3,5'-bis(hydroxymethyl)biphenyl-2,4'-diol
1333391-05-1

3',5-diallyl-3,5'-bis(hydroxymethyl)biphenyl-2,4'-diol

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 24h;63.15%
Honokiol
35354-74-6

Honokiol

3',5-aiallyl-3,5'-dinitro-[1,1'-biphenyl]-2,4'-diol

3',5-aiallyl-3,5'-dinitro-[1,1'-biphenyl]-2,4'-diol

Conditions
ConditionsYield
Stage #1: Honokiol With acetic acid In dichloromethane for 0.0833333h; Cooling with ice;
Stage #2: With nitric acid In dichloromethane at 0℃; for 6h;
61.3%
With nitric acid; acetic acid In dichloromethane at 10 - 20℃; for 1h;52%
Honokiol
35354-74-6

Honokiol

cyanomethyl bromide
590-17-0

cyanomethyl bromide

C22H20N2O2

C22H20N2O2

Conditions
ConditionsYield
With caesium carbonate; potassium iodide In acetone at 20℃; for 24h;61%
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