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Cas Database

10309-37-2

10309-37-2

Identification

  • Product Name:(+)-Bakuchiol

  • CAS Number: 10309-37-2

  • EINECS:

  • Molecular Weight:256.388

  • Molecular Formula: C18H24O

  • HS Code:2907199090

  • Mol File:10309-37-2.mol

Synonyms:Phenol,4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadien-1-yl]-;Bakuchiol(7CI);Phenol, 4-(3-ethenyl-3,7-dimethyl-1,6-octadienyl)-, [S-(E)]-;Phenol,4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadienyl]- (9CI);(S)-(+)-Bakuchiol;(S)-Bakuchiol;Drupanol;UP 256;BAKUCHIOL;Backuchiol;

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Safety information and MSDS view more

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:(S)-Bakuchiol
  • Packaging:2.5mg
  • Price:$ 160
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bakuchiol analytical standard
  • Packaging:10mg
  • Price:$ 230
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bakuchiol ≥95%
  • Packaging:20mg
  • Price:$ 253
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:4-(3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl)phenol 95+%
  • Packaging:1g
  • Price:$ 2016
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:4-(3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl)phenol 95+%
  • Packaging:250mg
  • Price:$ 908
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Bakuchiol
  • Packaging:003
  • Price:$ 900
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Bakuchiol
  • Packaging:002
  • Price:$ 450
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Bakuchiol >98%,StandardReferencesGrade
  • Packaging:20 mg
  • Price:$ 250
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  • Manufacture/Brand:Crysdot
  • Product Description:Bakuchiol 96%
  • Packaging:10mg
  • Price:$ 154
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  • Manufacture/Brand:ChemScene
  • Product Description:Bakuchiol 99.25%
  • Packaging:10mg
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Relevant articles and documentsAll total 10 Articles be found

Carnduff,Miller

, p. 606 (1967)

Synthesis of (±)-Bakuchiol via a pot-economy approach

Huang, Meng-Yuan,Chen, Long,Li, Ruoxi,Ji, Xueshun,Hong, Ran

, p. 715 - 720 (2014)

A rapid synthetic route toward (±)-Bakuchiol is presented in 29% overall yield. After the sole all-carbon quaternary carbon center is created via allylboration of 2-aryl acetaldehyde, a “Pot-Economy” approach including mesylation, elimination, and desilylation was realized in the presence oftBuOK under ambient temperature to provide (±)-Bakuchiol.

Carnduff,Miller

, p. 2671 (1968)

Enantioselective Synthesis of Quaternary Stereocenters via Chromium Catalysis

Xiong, Yang,Zhang, Guozhu

, p. 5094 - 5097 (2016/10/14)

Asymmetric allylation of aldehydes with γ-disubstituted allyl halides has been achieved in the presence of a sulfonamide/oxazoline chromium complex. A variety of synthetically useful α-homoallylic alcohols with two consecutive stereogenic centers, including one quaternary carbon, can be accessed in a highly diastereoselective and enantioselective manner.

A short synthesis of (+)-bakuchiol

Esumi, Tomoyuki,Yamamoto, Chihiro,Fukuyama, Yoshiyasu

, p. 1845 - 1847 (2013/09/12)

The concise enantioselective total synthesis of (+)-bakuchiol has been achieved using an asymmetric 1,4-addition to construct its all-carbon chiral quaternary center based on the induction of chirality by the (2′S)-2′-phenyloxazolidinone auxiliary, followed by a one-pot transformation under aldol reaction conditions. The synthesis was completed in four steps from (E)-geranic acid in an overall yield of 53%. Georg Thieme Verlag Stuttgart · New York.

A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol

Xu, Qian-Qian,Zhao, Qun,Shan, Guang-Sheng,Yang, Xi-Cheng,Shi, Qi-Yuan,Lei, Xinsheng

, p. 10739 - 10746 (2013/12/04)

A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol, and ent-Bakuchiol is described through one common intermediate bearing a chiral all-carbon quaternary carbon center, which involves stereoselectively unconjugated alkylation of the α,β-unsaturated imide bearing Evans' auxiliary, Takai-Utimoto reaction, Negishi reaction, and Heck reaction as key steps.

Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol

Takao, Ken-Ichi,Shu, Sakamoto,Touati, Marianne Ayaka,Kusakawa, Yusuke,Tadano, Kin-Ichi

, p. 13330 - 13344 (2013/02/23)

An asymmetric Claisen rearrangement using Oppolzer's camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.

Process route upstream and downstream products

Process route

trans-geranyl bromide
6138-90-5

trans-geranyl bromide

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: 3,4,5-trifluoro-N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; chromium dichloride; zirconocene dichloride; cesium iodide; nickel dichloride; manganese / tetrahydrofuran / 10 h / -10 °C / Inert atmosphere
2.1: pyridine; methanesulfonyl chloride / 10 h / 20 °C
2.2: 5 h / 20 °C
3.1: methyl magnesium iodide / 0.17 h / 185 °C / Inert atmosphere
With pyridine; chromium dichloride; manganese; methyl magnesium iodide; zirconocene dichloride; 3,4,5-trifluoro-N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; methanesulfonyl chloride; nickel dichloride; cesium iodide; In tetrahydrofuran;
4-Methoxyphenylacetaldehyde
5703-26-4

4-Methoxyphenylacetaldehyde

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: 3,4,5-trifluoro-N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; chromium dichloride; zirconocene dichloride; cesium iodide; nickel dichloride; manganese / tetrahydrofuran / 10 h / -10 °C / Inert atmosphere
2.1: pyridine; methanesulfonyl chloride / 10 h / 20 °C
2.2: 5 h / 20 °C
3.1: methyl magnesium iodide / 0.17 h / 185 °C / Inert atmosphere
With pyridine; chromium dichloride; manganese; methyl magnesium iodide; zirconocene dichloride; 3,4,5-trifluoro-N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; methanesulfonyl chloride; nickel dichloride; cesium iodide; In tetrahydrofuran;
(R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene
1020108-61-5

(R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene

4-[(1E,3R)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol
1020108-62-6

4-[(1E,3R)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol

Conditions
Conditions Yield
(R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene; With methyl magnesium iodide; In diethyl ether;
at 185 ℃; for 0.166667h; optical yield given as %ee; Inert atmosphere;
(S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene
17015-63-3,100428-91-9,10309-44-1

(S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene

4-[(1E,3R)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol
1020108-62-6

4-[(1E,3R)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol

Conditions
Conditions Yield
(S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene; With methyl magnesium iodide; In diethyl ether;
at 185 ℃; for 0.166667h; optical yield given as %ee; Inert atmosphere;
(R)-(-)-3-vinyl-3,7-dimethyloct-6-enal
1201917-34-1

(R)-(-)-3-vinyl-3,7-dimethyloct-6-enal

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: diethyl ether / 2 h / 0 °C / Inert atmosphere
2: pyridine; trichlorophosphate / 4 h / Inert atmosphere; Reflux
3: methyl magnesium iodide / diethyl ether / 0.25 h / 0 - 180 °C / Inert atmosphere
With pyridine; methyl magnesium iodide; trichlorophosphate; In diethyl ether;
4-methoxyphenyl magnesium bromide
13139-86-1

4-methoxyphenyl magnesium bromide

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: diethyl ether / 2 h / 0 °C / Inert atmosphere
2: pyridine; trichlorophosphate / 4 h / Inert atmosphere; Reflux
3: methyl magnesium iodide / diethyl ether / 0.25 h / 0 - 180 °C / Inert atmosphere
With pyridine; methyl magnesium iodide; trichlorophosphate; In diethyl ether;
(2R,3S)-1-(4-methoxyphenyl)-3,7-dimethyl-3-vinyloct-6-en-2-ol

(2R,3S)-1-(4-methoxyphenyl)-3,7-dimethyl-3-vinyloct-6-en-2-ol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: pyridine; methanesulfonyl chloride / 10 h / 20 °C
1.2: 5 h / 20 °C
2.1: methyl magnesium iodide / 0.17 h / 185 °C / Inert atmosphere
With pyridine; methyl magnesium iodide; methanesulfonyl chloride;
(2E)-3,7-dimethyl-2,6-octadienoyl chloride
58558-13-7

(2E)-3,7-dimethyl-2,6-octadienoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: lithium chloride
2: diethyl ether / -50 °C
3: hexamethyldisilazane / tetrahydrofuran / -78 °C
4: methyl magnesium iodide / 0.17 h / 160 °C
With methyl magnesium iodide; lithium chloride; In tetrahydrofuran; diethyl ether;
Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: triethylamine; pivaloyl chloride / tetrahydrofuran / -25 - -20 °C
2: lithium chloride
3: diethyl ether / -50 °C
4: hexamethyldisilazane / tetrahydrofuran / -78 °C
5: methyl magnesium iodide / 0.17 h / 160 °C
With methyl magnesium iodide; pivaloyl chloride; triethylamine; lithium chloride; In tetrahydrofuran; diethyl ether;
Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: diethyl ether / -50 °C
2: hexamethyldisilazane / tetrahydrofuran / -78 °C
3: methyl magnesium iodide / 0.17 h / 160 °C
With methyl magnesium iodide; In tetrahydrofuran; diethyl ether;

Global suppliers and manufacturers

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  • Hangzhou Dingyan Chem Co., Ltd
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  • Simagchem Corporation
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  • Amadis Chemical Co., Ltd.
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  • Shaanxi BLOOM TECH Co.,Ltd
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