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Cas Database

41442-57-3

41442-57-3

Identification

Synonyms:5-Heptadecylresorcinol;5-n-Heptadecylresorcinol

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Safety information and MSDS view more

  • Pictogram(s):2287460

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H319 Causes serious eye irritation

  • 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 view more

  • Manufacture/Brand
  • Product Description
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:5-Heptadecylresorcinol analytical standard
  • Packaging:10mg
  • Price:$ 602
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:5-Heptadecylresorcinol 95+%
  • Packaging:5mg
  • Price:$ 590
  • Delivery:In stock
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  • Manufacture/Brand:Arctom
  • Product Description:5-Heptadecylresorcinol ≥98%
  • Packaging:100mg
  • Price:$ 774
  • Delivery:In stock
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  • Manufacture/Brand:Arctom
  • Product Description:5-Heptadecylresorcinol ≥98%
  • Packaging:5mg
  • Price:$ 373
  • Delivery:In stock
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Relevant articles and documentsAll total 4 Articles be found

Synthesis and inhibitory activities against colon cancer cell growth and proteasome of alkylresorcinols

Zhu, Yingdong,Soroka, Dominique N.,Sang, Shengmin

, p. 8624 - 8631 (2012/11/13)

We have identified alkylresorcinols (ARs) as the major active components in wheat bran against human colon cancer cell growth (HCT-116 and HT-29) using a bioassay-guided approach. To further study the structure-activity relationships, 15 ARs and their intermediates (1-15) were synthesized expediently by the modified Wittig reaction in aqueous media, and six 5-alkylpyrogallols and their analogues (16-21) were prepared by the general Grignard reaction. The synthetic AR analogues were evaluated for activities against the growth of human colon cancer cells HCT-116 and HT-29 and the chymotrypsin-like activity of the human 20S proteasome. Our results found that (1) AR C13:0 and C15:0 (13 and 14) had the greatest inhibitory effects in human colon cancer cells HCT-116 and HT-29, while decreasing or increasing the side chain lengths diminished the activities; (2) two free meta-hydroxyl groups at C-1 and C-3 on the aromatic ring of the AR analogues greatly contributed to their antitumor activity; (3) the introduction of a third hydroxyl group at C-2 (20 and 21) into the aromatic ring of the AR analogues yielded no significant enhancement in activity against HCT-116 cells and decimated the effects against HT-29 cells, but dramatically increased the activity against the chymotrypsin-like activity of the human 20S proteasome; and (4) AR C11:0 (12) was found to have the greatest effect in a series of AR C9:0-C17:0 against the chymotrypsin-like activity of the human 20S proteasome.

An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

Parikka, Kirsti,Waehaelae, Kristiina

supporting information; experimental part, (2010/04/22)

The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C23 and C25 analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semistabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

Process route upstream and downstream products

Process route

1,3-dimethoxy-5-heptadecylbenzene
41395-17-9

1,3-dimethoxy-5-heptadecylbenzene

5-heptadecylresorcinol
41442-57-3

5-heptadecylresorcinol

Conditions
Conditions Yield
With boron tribromide; In dichloromethane; at 0 - 20 ℃;
95%
With boron tribromide; In dichloromethane; at -20 - 20 ℃;
39%
1,3-dimethoxy-5-heptadecylbenzene; With boron tribromide; In dichloromethane; at -70 ℃; for 5h;
With water; In dichloromethane; at 20 ℃;
1-(3',5'-Dimethoxyphenyl)heptadecan-1-ol
52483-25-7

1-(3',5'-Dimethoxyphenyl)heptadecan-1-ol

5-heptadecylresorcinol
41442-57-3

5-heptadecylresorcinol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 45 percent / Et3SiH / trifluoroacetic acid / 24 h / 45 °C
2: 39 percent / BBr3 / CH2Cl2 / -20 - 20 °C
With triethylsilane; boron tribromide; In dichloromethane; trifluoroacetic acid;
hexadecylmagnesium bromide
872-26-4

hexadecylmagnesium bromide

5-heptadecylresorcinol
41442-57-3

5-heptadecylresorcinol

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 62 percent / tetrahydrofuran / -20 - 20 °C
2: 69 percent / 2N KOH / 2 h / Heating
3: 45 percent / Et3SiH / trifluoroacetic acid / 24 h / 45 °C
4: 39 percent / BBr3 / CH2Cl2 / -20 - 20 °C
With triethylsilane; potassium hydroxide; boron tribromide; In tetrahydrofuran; dichloromethane; trifluoroacetic acid;
3,5-dimethoxybenzoyl chloride
17213-57-9

3,5-dimethoxybenzoyl chloride

5-heptadecylresorcinol
41442-57-3

5-heptadecylresorcinol

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 62 percent / tetrahydrofuran / -20 - 20 °C
2: 69 percent / 2N KOH / 2 h / Heating
3: 45 percent / Et3SiH / trifluoroacetic acid / 24 h / 45 °C
4: 39 percent / BBr3 / CH2Cl2 / -20 - 20 °C
With triethylsilane; potassium hydroxide; boron tribromide; In tetrahydrofuran; dichloromethane; trifluoroacetic acid;
3,5-Dimethoxy-benzoic acid 1-(3,5-dimethoxy-phenyl)-heptadecyl ester

3,5-Dimethoxy-benzoic acid 1-(3,5-dimethoxy-phenyl)-heptadecyl ester

5-heptadecylresorcinol
41442-57-3

5-heptadecylresorcinol

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 69 percent / 2N KOH / 2 h / Heating
2: 45 percent / Et3SiH / trifluoroacetic acid / 24 h / 45 °C
3: 39 percent / BBr3 / CH2Cl2 / -20 - 20 °C
With triethylsilane; potassium hydroxide; boron tribromide; In dichloromethane; trifluoroacetic acid;
S-(hydrogen malonyl)coenzyme A
524-14-1

S-(hydrogen malonyl)coenzyme A

[3H]-Stearoyl-Coenzyme A

[3H]-Stearoyl-Coenzyme A

C<sub>22</sub>H<sub>38</sub>O<sub>3</sub>
889131-93-5

C22H38O3

5-heptadecylresorcinol
41442-57-3

5-heptadecylresorcinol

dihydromerulinic acid A

dihydromerulinic acid A

Conditions
Conditions Yield
With alkylresorcylic acid synthase, ARAS1; at 30 ℃; for 0.333333h; pH=7; Kinetics; aq. phosphate buffer; Enzymatic reaction;
5-heptadecylresorcinol
41442-57-3

5-heptadecylresorcinol

Conditions
Conditions Yield
5-Heptadecylresorcinoldimethylester, BBr3; Demethylierung;
2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide
21149-38-2

2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide

5-heptadecylresorcinol
41442-57-3

5-heptadecylresorcinol

C<sub>29</sub>H<sub>56</sub>O<sub>2</sub>Si<sub>2</sub>

C29H56O2Si2

Conditions
Conditions Yield
With pyridine; In chloroform; at 80 ℃; for 0.333333h;
5-heptadecylresorcinol
41442-57-3

5-heptadecylresorcinol

[2,4,6-2H<sub>3</sub>]-5-heptadecylresorcinol
1108148-88-4

[2,4,6-2H3]-5-heptadecylresorcinol

Conditions
Conditions Yield
With diclazuril; microwave irradiation;

Global suppliers and manufacturers

Global( 12) Suppliers
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  • Leader Biochemical Group
  • Business Type:Lab/Research institutions
  • Contact Tel:86-029-68895030
  • Emails:info@leader-biogroup.com
  • Main Products:65
  • Country:China (Mainland)
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:1
  • Country:China (Mainland)
  • BioBioPha Co., Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-871-65217109
  • Emails:sales@mail.biobiopha.com
  • Main Products:1
  • Country:China (Mainland)
  • NovaChemistry
  • Business Type:Trading Company
  • Contact Tel:+44 (0)208 191 7890
  • Emails:info@novachemistry.com
  • Main Products:1
  • Country:United Kingdom
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