136-77-6 Usage
Uses
Different sources of media describe the Uses of 136-77-6 differently. You can refer to the following data:
1. p-Hexylresorcinol shows antiimnflammatory activity acting on the human 5-LO (5-Lipoxygenase) proinflammatory enzyme.
2. anthelmintic, topical antiseptic
3. 4-Hexylresorcinol is an inhibitor of transglutaminase-2 in KB cells. Studies indicate that 4-Hexylresorcinol reduces DNA oxidative damage in human lymphocytes. is a substituted dihydroxybenzene used topically as an antiseptic for the treatment of minor skin infections. is a substituted phenol with bactericidal, antihelminthic and potential antineoplastic activities. The combination of 4-Hexylresorcinol and Cisplatin has been shown to inhibit tumor growth, cell growth, and KB cell viability.
4. 4-Hexylresorcinol is used as the starting material to synthesize a potent immune suppressor, celastramycin A. It is a precursor to prepare resorcinol-sn-glycerol derivatives, that exhibit high affinity for cannabinoid type 1 receptor. It can also be incorporated as a linker while building catenanes.
Chemical Properties
slightly red powder
General Description
Pale-yellow viscous liquid (that becomes solid on standing at room temperature) or a peach colored powder. Pungent faintly fatty odor. Sharp astringent taste.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
4-Hexyl-1,3-benzenediol may be sensitive to prolonged exposure to light. Incompatible with acid chlorides, acid anhydrides and oxidizing agents .
Hazard
Irritant to respiratory tract and skin, concentrated solutions are vesicant.
Fire Hazard
Flash point data for 4-Hexyl-1,3-benzenediol are not available. 4-Hexyl-1,3-benzenediol is probably combustible.
Biological Activity
hexylresorcinol is a mushroom tyrosinase inhibitor.tyrosinase, a copper-containing enzyme, is distributed in microorganisms, animals, and plants widely. mushroom tyrosinase has been becoming popular due to its availability and usages in various applications.
Clinical Use
4-Hexylresorcinol, or “hexylresorcinol,” is a white crystallinesubstance with a faint phenolic odor. When appliedto the tongue it produces a sensation of numbness. It isfreely soluble in alcohol but only slightly soluble in water(1–20,000 parts). Hexylresorcinol is an effective antiseptic,possessing both bactericidal and fungicidal properties.The phenol coefficient of hexylresorcinol against S. aureusis 98. As is typical for alkylated phenols, hexylresorcinolpossesses surfactant properties. The compound also haslocal anesthetic activity. Hexylresorcinol is formulatedinto throat lozenges because of its local anesthetic and antisepticproperties. These preparations are probably of littlevalue. Hexylresorcinol (in the concentration in thelozenge) is probably not antiseptic, and the local anestheticproperty can anesthetize the larynx, causing temporarylaryngitis.
in vitro
previous results showed hexylresorcinol could inhibit both mono- and di-phenolase activity of mushroom tyrosinase. moreover, hexylresorcinol at 2 μm lengthened the lag period from 98 s to 26. hexylresorcinol could also display reversible inhibition of the enzyme. in addition, the kinetic analyses showed that hexylresorcinol was a competitive inhibitor with the apparent inhibition constant binding with free enzyme to be 0.443 μm for diphenolase [1].
in vivo
previous in vivo study showed that hexylresorcinol could induce chromosome aberrations in mouse eukaryotic cells at doses of 0.5, 0.05, and 0.005 mg/g and the metabolic transformation of hexylresorcinol decreased its genotoxic effect in mice. moreover, the mutagenic effect lasted for 3 days only at the highest dose of hexylresorcinol (0.5 mg/g). thus, hexylresorcinol doses less than 0.5 mg/g were metabolized within two days to the extent of the cytotoxic effect. in addition, hexylresorcinol was transformed at a rate of 0.0025–0.025 mg/day after a single administration to mice [2].
IC 50
1.24 μm
references
[1] chen qx,ke ln,song kk,huang h,liu xd. inhibitory effects of hexylresorcinol and dodecylresorcinol on mushroom (agaricus bisporus) tyrosinase. protein j.2004 feb;23(2):135-41.[2] margulis ab,ozhiganova iv,bushmanova ov,kolpakov ai,il'inskaia on. hexylresorcinol induces chromosome aberrations in mouse peripheral blood cells. genetika. 2005 aug;41(8):1045-8.
Check Digit Verification of cas no
The CAS Registry Mumber 136-77-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 6 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 136-77:
(5*1)+(4*3)+(3*6)+(2*7)+(1*7)=56
56 % 10 = 6
So 136-77-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H18O2/c1-2-3-4-5-6-10-7-11(13)9-12(14)8-10/h7-9,13-14H,2-6H2,1H3
136-77-6Relevant articles and documents
Nematic phase formed by V-shaped molecules
Szydlowska, Jadwiga,Matraszek, Joanna,Mieczkowski, Jozef,Gorecka, Ewa,Pociecha, Damian
, p. 107 - 115 (2001)
In the paper there are presented synthesis and properties of new banana-shaped molecules that are ester resorcinol derivatives. The compounds with lateral alkyl substituent at the 4-position of the resorcinol ring exhibit the liquid crystalline nematic phase. Some of the synthesised compounds are able to induce the anticlinic S*CA phase that proves their bent molecular shape.
Preparation method of 4-alkylresorcinol
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Paragraph 0053-0055; 0059-0060, (2021/11/03)
The invention discloses a preparation method of 4-alkyl resorcinol, and belongs to the field of organic synthetic chemistry. The method comprises the following steps: carrying out Claisen-Schmidt condensation reaction on 4-acetyl resorcinol and alkyl aldehyde to obtain an intermediate III, and carrying out catalytic hydrogenation reduction to obtain 4-alkyl resorcinol; the synthetic reaction route of the method is as follows: raw and auxiliary materials and reagents used in the method are low in toxicity, safe, low in price and easy to obtain; the yield is obviously improved, byproducts are reduced, and the production cost is reduced; high-toxicity and high-pollution reagents are prevented from being used in the reduction process, and environmental protection is achieved; different 4-alkyl resorcinol can be obtained by using alkyl aldehydes with different carbon atom numbers; the product prepared by the method is high in quality, and the method has a significant meaning for industrial production of 4-alkylresorcinol.
Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists
Liu, Peng,Xu, Xing,Chen, Lili,Ma, Lei,Shen, Xu,Hu, Lihong
, p. 1596 - 1607 (2014/03/21)
Compound 1 (IC50 = 35.2 ± 7.2 μM), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 ± 0.1 μM. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity.
Process for the synthesis of alkylresorcinols
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Page/Page column 3, (2008/06/13)
The invention provides a process for the production of 4-(C2-C16)alkylresorcinol. 4-(C2-C16)alkylresorcinol is produced by reacting resorcinol with a (C2-C16)alkyloic acid in the presence of a zinc chloride catalyst to produce an intermediate comprising a 4-(C2-C16)acylresorcinol and zinc ions. Then the intermediate is adjusted such that the zinc ion content is from about 0.1 to about 150 parts per million based on the weight of the intermediate to form an adjusted intermediate. Then the produced 4-(C2-C16)acylresorcinol is hydrogenated in the presence of the zinc ions and a base metal hydrogenation catalyst to produce a crude product comprising 4-(C2-C16)alkylresorcinol, which may thereafter be isolated.
