Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces and more

Bamboo, Beech, Paracetamol, Plant Toxins, Spruce, Sticks and Stones

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2 years ago

Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces and more

Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces (Picea abies). Picein is the glucoside of piceol.

Løkke, H. (1990). “Picein and piceol concentrations in Norway spruce”. Ecotoxicology and Environmental Safety. 19 (3): 301–9. doi:10.1016/0147-6513(90)90032-z. PMID 2364913.
Münzenberger, Babette; Heilemann, Jürgen; Strack, Dieter; Kottke, Ingrid; Oberwinkler, Franz (1990). “Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce”. Planta. 182 (1): 142–8. doi:10.1007/BF00239996. PMID 24197010.
Løkke, Hans (1990). “Picein and piceol concentrations in Norway spruce”. Ecotoxicology and Environmental Safety. 19 (3): 301–309. doi:10.1016/0147-6513(90)90032-Z. PMID 2364913.
U.S. Patent 4,524,217
Münzenberger, Babette; Heilemann, Jürgen; Strack, Dieter; Kottke, Ingrid; Oberwinkler, Franz (1990). “Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce”. Planta. 182 (1): 142–8. doi:10.1007/BF00239996. PMID 24197010. S2CID 43504838.

Pungenin is a also phenolic compound found in the needles of Blue Spruce (Picea pungens). It is the glucoside of 3,4-dihydroxyacetophenone. The compound serves a feeding deterrent against Spruce Budworm larvae.

Neish, A. C. (1957). “Pungenin: a Glucoside found in the leaves of Picea Pungens (Colorado Spruce)”. Canadian Journal of Biochemistry and Physiology. 35 (2): 161–167. doi:10.1139/o57-020. PMID 13404533.
Strunz, George M.; Giguère, Pierre; Thomas, Anthony W. (1986). “Synthesis of pungenin, a foliar constituent of some spruce species, and investigation of its efficacy as a feeding deterrent for spruce budworm [Choristoneura fumiferana (Clem.)]”. Journal of Chemical Ecology. 12 (1): 251–260. doi:10.1007/BF01045608. PMID 24306414. S2CID 28774331.

This may be a little redundant as the base information is already included on the Baccharis page but I want to flesh out a few of the mentions.

Uses

Piceol can be used to make acetaminophen by oxime formation with hydroxylamine and subsequent Beckmann rearrangement in acid. An industrial synthesis of paracetamol (acetaminophen) developed by Hoechst–Celanese involves the conversion of a methyl ketone to an acetanilide via a Beckmann rearrangement.

U.S. Patent 4,524,217
US patent 5155273, Fritch, John R. (Corpus Christi, TX); Fruchey, Stanley O. (Bad Soden/T.S., DE); Horlenko, Theodore (Corpus Christi, TX); Aguilar, Daniel A. (Corpus Christi, TX); Hilton, Charles B. (Corpus Christi, TX); Snyder, Phillip S. (Rock Hill, SC); Seeliger, William J. (Corpus Christi, TX), “Production of acetaminophen”, published 13 October 1992, assigned to Hoechst Celanese Corporation (Somerville, NJ)

Piceol is used in the synthesis of several pharmaceutical drugs including octopamine, sotalol, bamethan, and dyclonine.^{[citation needed]} We really need that citation because I looked up these drugs and wtf.

Anticonvulsants are also possible by Mannich reaction.

Keshari, Amit K.; Tewari, Aseem; Verma, Shweta S.; Saraf, Shailendra K. (2017). “Novel Mannich-bases as Potential Anticonvulsants: Syntheses, Characterization and Biological Evaluation”. Central Nervous System Agents in Medicinal Chemistry. 17 (3). doi:10.2174/1871524917666170717113524. ISSN 1871-5249.

Metabolism

Diprenylated derivatives of piceol can be isolated from Ophryosporus macrodon (a genus of South American flowering plants in the tribe Eupatorieae).

Sigstad, Elizabeth; Catalán, César A.N.; Diaz, Jesús G.; Herz, Werner (1993). “Diprenylated derivatives of p-hydroxyacetophenone from Ophryosporus macrodon”. Phytochemistry. 33: 165–169. doi:10.1016/0031-9422(93)85415-N.

4-Hydroxyacetophenone monooxygenase is an enzyme that transforms piceol into O-acetylhydroquinone. This enzyme is found in Pseudomonas fluorescens (and that definitely needs its own page).

p-Hydroxyacetophenone (p-HAP) and its glucoside picein are plant-derived natural products that have been extensively used in chemical, pharmaceutical and cosmetics. Found in Ficus erecta var. beecheyana, Artemisia ordosica, and other organisms. P-HAP aka 4′-hydroxyacetophenone is a monohydroxyacetophenone carrying a hydroxy substituent at position 4′. It has a role as a plant metabolite, a fungal metabolite and a mouse metabolite. In this study, they designed and constructed a biosynthetic pathway for de novo production of p-HAP and picein from glucose in E. coli.

https://www.wikidata.org/wiki/Q7190613
National Center for Biotechnology Information. “PubChem Compound Summary for CID 7469, 4′-Hydroxyacetophenone” PubChem, https://pubchem.ncbi.nlm.nih.gov/compound/4_-Hydroxyacetophenone. Accessed 10 April, 2023.
Lu L, Wang X, Zhou L, Liu Q, Zhang G, Xue B, Hu C, Shen X, Sun X, Yan Y, Wang J, Yuan Q. Establishing biosynthetic pathway for the production of p-hydroxyacetophenone and its glucoside in Escherichia coli. Metab Eng. 2023 Mar;76:110-119. doi: 10.1016/j.ymben.2023.02.001. Epub 2023 Feb 4. PMID: 36746296.

Paroxypropione, where the acetyl group is replaced by a propionyl group.
- Paroxypropione, also known as paraoxypropiophenone, is a syntheticnonsteroidal estrogen which has been used medically as an antigonadotropin in Spain and Italy but appears to no longer be marketed. It was first synthesized in 1902. The antigonadotropic properties of the drug were discovered in 1951 and it entered clinical use shortly thereafter. Paroxypropione is closely related structurally to p-hydroxybenzoic acid and parabens such as methylparaben, and also bears a close resemblance to diethylstilbestrol (which, in fact, produces paroxypropione as an active metabolite) and alkylphenols like nonylphenol, all of which are also estrogens. The drug possesses relatively low affinity for the estrogen receptor and must be given at high dosages to achieve significant estrogenic and antigonadotropic effects, for instance, 0.8 to 1.6 g/day. It possesses 0.1% of the estrogenic activity and less than 0.5% of the antigonadotropic potency of estrone. Derivatives – Paroxypropione is a precursor in the chemical synthesis of diethylstilbestrol and dienestrol. Well shit. Brand names Frenantol, Frenormon, Hypophenon, Paroxon, Possipione, Profenone, numerous others; former developmental code name NSC-2834), also known as paroxypropiophenone (P.O.P.) or 4′-hydroxypropiophenone. Research – Paroxypropione was studied and used in the treatment of breast cancer.. Synthesis – The highest reported yield, approximately 96%, is from the between phenol and propionyl chloride. The mechanism is likely to involve initial esterification to give phenyl propionate, which then undergoes a Fries rearrangement.
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  - Paulsen CA, Mortimore GE, Heller CG (August 1951). “The pituitary action and estrogenic effect of parahydroxy-propiophenone”. The Journal of Clinical Endocrinology and Metabolism. 11 (8): 892–4. doi:10.1210/jcem-11-8-892. PMID 14861299.
  - Mombelli E (January 2012). “Evaluation of the OECD (Q)SAR Application Toolbox for the profiling of estrogen receptor binding affinities”. SAR and QSAR in Environmental Research. 23 (1–2): 37–57. doi:10.1080/1062936X.2011.623325. PMID 22014213. S2CID 19751228.
  - Buu-Hoi NP, Xuong ND, Lavit D (1953). “Fluorine-containing analogs of 4-hydroxypropiophenone”. The Journal of Organic Chemistry. 18 (8): 910–915. doi:10.1021/jo50014a002. ISSN 0022-3263.
  - Chambers PL, Günzel P (12 March 2013). Mechanism of Toxic Action on Some Target Organs: Drugs and Other Substances. Springer Science & Business Media. pp. 276–. ISBN 978-3-642-67265-1.
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  - Jones RE, Lopez KH (28 September 2013). Human Reproductive Biology. Academic Press. pp. 46–. ISBN 978-0-12-382185-0.
  - Pugazhendhi D, Pope GS, Darbre PD (2005). “Oestrogenic activity of p-hydroxybenzoic acid (common metabolite of paraben esters) and methylparaben in human breast cancer cell lines”. Journal of Applied Toxicology. 25 (4): 301–9. doi:10.1002/jat.1066. PMID 16021681. S2CID 12342018.
  - De Vega R (1955). “Protein breakdown before and after operations. Influence of growth hormone and of inhibitors of the pituitary adrenal system”. Cirug., Ginecol. Urol. 9: 289–326.
  - Bussolati C, de Carneri I, Castellino S, Marinoni V, Sperzani GL (July 1967). “Treatment of experimental and clinical schistosomiasis with hormonal inhibitors of ovulation”. The American Journal of Tropical Medicine and Hygiene. 16 (4): 497–9. doi:10.4269/ajtmh.1967.16.497. PMID 5006470.^{[permanent dead link]}
  - Scott CC, Kroc RL, Stasilli NR (June 1952). “Metabolic and toxicity studies on parahydroxypropiophenone”. Endocrinology. 50 (6): 607–11. doi:10.1210/endo-50-6-607. PMID 12980070.
  - Murashige R, Hayashi Y, Ohmori S, Torii A, Aizu Y, Muto Y, Murai Y, Oda Y, Hashimoto M (2011). “Comparisons of O-acylation and Friedel–Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonicacid: effective synthesis of optically active homotyrosines”. Tetrahedron. 67 (3): 641–649. doi:10.1016/j.tet.2010.11.047. hdl:2115/44794.
  - William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1286, 1290. ISBN 978-0-8155-1856-3.
  - Szmant HH (1989). Organic Building Blocks of the Chemical Industry. John Wiley & Sons. pp. 532–. ISBN 978-0-471-85545-3.
  - Maconi G (June 1955). “[Hydroxypropiophenone in the therapy of metastases of carcinoma of the breast]” [Hydroxypropiophenone in the therapy of metastases of carcinoma of the breast]. Il Farmaco; Edizione Pratica (in Italian). 10 (6): 291–9. PMID 13241536.
  - Stoll BA (August 1956). “P-hydroxypropiophenone for advanced breast cancer: a preliminary report”. The Medical Journal of Australia. 43 (5): 181–3. doi:10.5694/j.1326-5377.1956.tb56562.x. PMID 13358357. S2CID 22364847.
  - Grapulin G (June 1967). “[Experience with paraoxypropiophenone (Frenantol) in the treatment of dysplasias and metastasized carcinoma of the breast]” [Experience with paraoxypropiophenone (Frenantol) in the treatment of dysplasias and metastasized carcinoma of the breast]. Chirurgia Italiana (in Italian). 19 (3): 306–12. PMID 5188348.
  - Gustavo RP (July 1958). “[Anti-gonadotropic action of possipione]” [Anti-gonadotropic action of possipione]. Quaderni di Clinica Ostetrica e Ginecologica (in Italian). 13 (7): 307–15. PMID 13579130.
Apocynin
- Apocynin, also known as acetovanillone, is a natural organic compound structurally related to vanillin. It has been isolated from a variety of plant sources and is being studied for its variety of pharmacological properties. Apocynin was first described in 1883 by Oswald Schmiedeberg, (1838 – 1921) a Baltic German pharmacologist. (Interesting bio information: In 1911, he testified in the United States v. Forty Barrels and Twenty Kegs of Coca-Cola trial, and later, was a major factor in the success of the German pharmaceutical industry prior to the Second World War, having trained most of the European professors at the time. See more below.) Apocynin was first isolated by Horace Finnemore, in 1908, from the root of Canadian hemp (Apocynum cannabinum). At the time, this plant was already used for its known effectiveness against edema and heart problems. In 1971, apocynin was also isolated from Picrorhiza kurroa, a small plant that grows at high altitudes in the western Himalayas. P. kurroa was used for ages as a treatment for liver and heart problems, jaundice, and asthma. In 1990, Simons et al. isolated apocynin to a pharmacologically useful level using an actively guided isolation procedure. Apocynin’s observed anti-inflammatory capabilities proved to be a result of its ability to selectively prevent the formation of free radicals, oxygen ions, and peroxides in the body. Apocynin has since been extensively studied to help determine its disease-fighting capabilities and applications.^{[citation needed]} NADPH oxidase is an enzyme that effectively reduces O₂ to superoxide (O₂^–•), which can be used by the immune system to kill bacteria and fungi. Apocynin is an inhibitor of NADPH oxidase activity and thus is effective in preventing the production of the superoxide in human white blood cells or neutrophilic granulocytes. It does not however obstruct the phagocytic or other defense roles of granulocytes. Due to the selectivity of its inhibition, apocynin can be widely used as an inhibitor of NADPH oxidase without interfering in other aspects of the immune system.^{[citation needed]} Apocynin was used to determine whether ionic activation due to proton flux across the membrane of renal medulla cells was coupled to NADPH oxidase production of superoxide. Apocynin was introduced to the cells and completely blocked the production of superoxide, and was a key component in determining that the proton outflow was responsible for the activation of NADPH oxidase. The mechanism of action of apocynin is not understood. In the experimental studies, apocynin is shown to dimerize and form diapocynin. Although, diapocynin seems to have beneficial effect in reducing reactive oxygen species and anti-inflammatory properties, it is still yet to be shown as biologically relevant molecule. Biotransformation of apocynin predominantly leads to glycosylated form of apocynin. Another molecule that is shown to form under experimental conditions is nitroapocynin. Apocynin is a solid with a melting point of 115 °C and the faint odor of vanilla. It is soluble in hot water, alcohol, benzene, chloroform, and ether.^{[citation needed]}
  - Paech, K.; Tracey, M. V. (2012-12-06). Acetovanillone. pp. 410–1. ISBN 9783642649585. in de Stevens, George; Nord, F. F. (1955). “Natural Phenylpropane Derivatives”. In Paech, K.; Tracey, M. V. (eds.). Moderne Methoden der Pflanzenanalyse / Modern Methods of Plant Analysis. Springer-Verlag Berlin Heidelberg. pp. 392–427. doi:10.1007/978-3-642-64958-5_10. ISBN 978-3-642-64958-5.
  - Horace, Finnemore (1908). “The Constituents of Canadian Hemp. Part I. Apocynin”. Journal of the Chemical Society. 93 (2): 1513–9. doi:10.1039/ct9089301513. Retrieved 10 April 2014.
  - Li N, Zhang G, Yi FX, Zou AP, Li PL (2005). “Activation of NAD(P)H oxidase by outward movements of H+ ions in renal medullary thick ascending limb of Henle”. American Journal of Physiology. Renal Physiology. 289 (5): F1048–56. doi:10.1152/ajprenal.00416.2004. PMID 15972387.
  - Luchtefeld, Ron; Dasari, Mina S.; Richards, Kristy M.; Alt, Mikaela L.; Crawford, Clark F. P.; Schleiden, Amanda; Ingram, Jai; Hamidou, Abdel Aziz Amadou; Williams, Angela; Chernovitz, Patricia A.; Sun, Grace Y.; Luo, Rensheng; Smith, Robert E. (2008). “Synthesis of Diapocynin”. Journal of Chemical Education. 85 (3): 411. Bibcode:2008JChEd..85..411D. doi:10.1021/ed085p411.
  - Chandasana H, Chhonker YS, Bala V, Prasad YD, Chaitanya TK, Sharma VL, Bhatta RS (2015). “Pharmacokinetic, bioavailability, metabolism and plasma protein binding evaluation of NADPH-oxidase inhibitor apocynin using LC-MS/MS”. Journal of Chromatography B. 985: 180–8. doi:10.1016/j.jchromb.2015.01.025. PMID 25682338.
  - Babu S, Raghavamenon AC, Fronczek FR, Uppu RM (2009). “4-Hydr-oxy-3-meth-oxy-5-nitro-aceto-phenone (5-nitro-apocynin)”. Acta Crystallographica E. 65 (Pt 9): o2292–3. doi:10.1107/S160053680903390X. PMC 2969931. PMID 21577684.
  - Clinical trial number NCT01402297 for “Hydrogen Peroxide and Nitrite Reduction in Exhaled Breath Condensate of COPD Patients” at ClinicalTrials.gov
  - Stefanska J, Sarniak A, Wlodarczyk A, Sokolowska M, Pniewska E, Doniec Z, Nowak D, Pawliczak R (2012). “Apocynin reduces reactive oxygen species concentrations in exhaled breath condensate in asthmatics”. Experimental Lung Research. 38 (2): 90–9. doi:10.3109/01902148.2011.649823. PMID 22296407. S2CID 207441506.
  - T Hart BA, Simons JM, Knaan-Shanzer S, Bakker NP, Labadie RP (1990). “Antiarthritic activity of the newly developed neutrophil oxidative burst antagonist apocynin”. Free Radical Biology & Medicine. 9 (2): 127–31. doi:10.1016/0891-5849(90)90115-Y. PMID 2172098. INIST:19326251.
  - Palmen, M.J.H.J.; Beukelman, C.J.; Mooij, R.G.M.; Pena A.S.; van Rees, E.P. (1995). “Anti-inflammatory effect of apocynin, a plant-derived NADPH oxidase antagonist, in acute experimental colitis”. The Netherlands Journal of Medicine. 47 (2): 41. doi:10.1016/0300-2977(95)97051-P.
  - Van den Worm E, Beukelman CJ, Van den Berg AJ, Kroes BH, Labadie RP, Van Dijk H (2001). “Effects of methoxylation of apocynin and analogs on the inhibition of reactive oxygen species production by stimulated human neutrophils”. European Journal of Pharmacology. 433 (2–3): 225–30. doi:10.1016/S0014-2999(01)01516-3. PMID 11755156.
  - Harraz MM, Marden JJ, Zhou W, Zhang Y, Williams A, Sharov VS, Nelson K, Luo M, Paulson H, Schöneich C, Engelhardt JF (2008). “SOD1 mutations disrupt redox-sensitive Rac regulation of NADPH oxidase in a familial ALS model”. The Journal of Clinical Investigation. 118 (2): 659–70. doi:10.1172/JCI34060. PMC 2213375. PMID 18219391.
  - Liu N, Matsumura H, Kato T, Ichinose S, Takada A, Namiki T, Asakawa K, Morinaga H, Mohri Y, De Arcangelis A, Geroges-Labouesse E, Daisuke Nanba D, Nishimura EK (2019). “Stem cell competition orchestrates skin homeostasis and ageing”. Nature. 568 (7752): 344–350. doi:10.1038/s41586-019-1085-7. PMID 30944469. S2CID 92997308.
  - Oswald Schmiedeberg
    - In 1866 he earned his medical doctorate from the University of Dorpat with a thesis concerning the measurement of chloroform in blood, before becoming the first professor of pharmacology at the University of Strasbourg, where he remained for 46 years. His work largely dealt with chemicals poisonous to the heart, causing vomiting and those causing passing urine, as well as hypnotics, venoms and metals. Go figure. With his pupil Hans Horst Meyer he discovered glucuronic acid as a conjugation partner in xenobiotic metabolism and later found that glucuronic acid was also a component of cartilage and occurred as a disaccharide of chondroitin sulfate. He studied the composition of hyaluronic acid and explored its relationship to collagen, amyloid and chondroitin sulfate. In 1869 he demonstrated that muscarine had a similar effect on the heart as electrical stimulation of the vagus nerve. He also demonstrated the hypnotic properties of urethane.^{[citation needed]} He published over 200 scientific books and articles and with pathologists Bernhard Naunyn (1839–1925) and Edwin Klebs (1834–1913), he co-founded the journal Naunyn-Schmiedeberg’s Archives of Pharmacology.
    - Muscholl, E. (1 October 1995). “The evolution of experimental pharmacology as a biological science: the pioneering work of Buchheim and Schmiedeberg1”. British Journal of Pharmacology. 116 (4): 2155–2159. doi:10.1111/j.1476-5381.1995.tb15047.x. ISSN 1476-5381. PMC 1908990. PMID 8564242.
    - “Oswald Schmiedeberg (1838-1921) Experimental Pharmacologist”. Journal of the American Medical Association. 204 (10): 924–925. 3 June 1968. doi:10.1001/jama.1968.03140230082018. ISSN 0098-7484. PMID 4869651.
    - Bäumer, Beatrix (2007). “Schmiedeberg, Oswald”. Neue Deutsche Biographie (in German). Vol. 23. pp. 227–228.
    - Patil, Popat N. (2012). Discoveries in Pharmacological Sciences. Singapore: World Scientific. pp. 239–240. ISBN 978-981-4355-08-7.
    - Koch-Weser, J.; Schechter, P. J. (April 1978). “Schmiedeberg in Strassburg 1872-1918: the making of modern pharmacology”. Life Sciences. 22 (13–15): 1361–1371. doi:10.1016/0024-3205(78)90099-1. ISSN 0024-3205. PMID 351320.(subscription required)
    - Muscholl, E. (2001). “Schmiedeberg, Oswald”. Encyclopedia of Life Sciences. eLS. American Cancer Society. doi:10.1038/npg.els.0003617. ISBN 978-0-470-01590-2.
    - Agriculture, United States Department of (1912). Notice of Judgement, Food and Drug Act. pp. 56–57.
    - Pendergrast, Mark (2013). For God, Country, and Coca-Cola. Basic Books. ISBN 978-0-465-04699-7.
    - The United States, Appellant, Vs. Forty Barrels and Twenty Kegs, Coca-Cola, Appellee: From the District Court of the United States, Southern Division, Eastern District of Tennessee. Record, Part 1-4. James B. Cox … W.B. Miller … for Appellant; J.B. Sizer … Harold Hirsch … for Appellee. Macgowan-Cooke. 1912.
    - “A brief history of pharmacology”. Modern Drug Discovery, American Chemical Society. 2001. Retrieved 2 April 2007.
    - Meyer, Hans H. (1922). “Oswald Schmiedeberg”. Die Naturwissenschaften. 10 (5): 105–107. Bibcode:1922NW…..10..105M. doi:10.1007/BF01488534. S2CID 35518685.
    - Bäumer Beatrix (2007), “Schmiedeberg, Johann Ernst Oswald”, Neue Deutsche Biographie (in German), vol. 23, Berlin: Duncker & Humblot, pp. 227–228
    - Selected publications
      - Ueber die quantitative bestimmung des Chloroforms im Blute und sein Verhalten gegen dasselbe. 1866 – On the quantitative determination of chloroform in the blood, etc.
      - Das Muscarin. Das giftige Alkaloid des Fliegenpilzes (Agaricus muscarius L.) seine Darstellung, chemischen Eigenschaften, physiologischen Wirkungen, toxicologische Bedeutung und sein Verhältniss zur Pilzvergiftung im allgemeine, 1869 – Muscarine. The poisonous alkaloid of fly agaric mushroom, its representation, chemical properties, physiological effects, etc.
      - Grundriss der Arzneimittellehre, 1883 – Fundamentals of pharmacology.
      - “The dietetic and therapeutic uses of ferratin“; published in English (1893).
      - “Ferratin : the ferruginous element of food”; published in English (1894).
      - Grundriss der Pharmakologie in Bezug auf Arzneimittellehre und Toxikologie, 1902 Digital 5th edition from 1906 by the University and State Library Düsseldorf
      - Arzneimittel und genussmittel, Salzwasser (1912). Digital edition by the University and State Library Düsseldorf
      - Über die Pharmaka in der Ilias und Odyssee. Karl J. Trubner, Strasburg (1918). Digital edition by the University and State Library Düsseldorf

References

Løkke, H. (1990). “Picein and piceol concentrations in Norway spruce”. Ecotoxicology and Environmental Safety. 19 (3): 301–9. doi:10.1016/0147-6513(90)90032-z. PMID 2364913.
Münzenberger, Babette; Heilemann, Jürgen; Strack, Dieter; Kottke, Ingrid; Oberwinkler, Franz (1990). “Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce”. Planta. 182 (1): 142–8. doi:10.1007/BF00239996. PMID 24197010.
Løkke, Hans (1990). “Picein and piceol concentrations in Norway spruce”. Ecotoxicology and Environmental Safety. 19 (3): 301–309. doi:10.1016/0147-6513(90)90032-Z. PMID 2364913.
U.S. Patent 4,524,217
Keshari, Amit K.; Tewari, Aseem; Verma, Shweta S.; Saraf, Shailendra K. (2017). “Novel Mannich-bases as Potential Anticonvulsants: Syntheses, Characterization and Biological Evaluation”. Central Nervous System Agents in Medicinal Chemistry. 17 (3). doi:10.2174/1871524917666170717113524. ISSN 1871-5249.
Sigstad, Elizabeth; Catalán, César A.N.; Diaz, Jesús G.; Herz, Werner (1993). “Diprenylated derivatives of p-hydroxyacetophenone from Ophryosporus macrodon”. Phytochemistry. 33: 165–169. doi:10.1016/0031-9422(93)85415-N.

Chemical compound p-Hydroxyacetophenone found in:

Categories:

Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces and more

Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces (Picea abies). Picein is the glucoside of piceol.

Pungenin is a also phenolic compound found in the needles of Blue Spruce (Picea pungens). It is the glucoside of 3,4-dihydroxyacetophenone. The compound serves a feeding deterrent against Spruce Budworm larvae.

This may be a little redundant as the base information is already included on the Baccharis page but I want to flesh out a few of the mentions.

Uses

Piceol is used in the synthesis of several pharmaceutical drugs including octopamine, sotalol, bamethan, and dyclonine.^{[citation needed]} We really need that citation because I looked up these drugs and wtf.

Anticonvulsants are also possible by Mannich reaction.

Metabolism

Diprenylated derivatives of piceol can be isolated from Ophryosporus macrodon (a genus of South American flowering plants in the tribe Eupatorieae).

4-Hydroxyacetophenone monooxygenase is an enzyme that transforms piceol into O-acetylhydroquinone. This enzyme is found in Pseudomonas fluorescens (and that definitely needs its own page).

See also

References

Chemical compound p-Hydroxyacetophenone found in:

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Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces and more

Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces (Picea abies). Picein is the glucoside of piceol.

Pungenin is a also phenolic compound found in the needles of Blue Spruce (Picea pungens). It is the glucoside of 3,4-dihydroxyacetophenone. The compound serves a feeding deterrent against Spruce Budworm larvae.

This may be a little redundant as the base information is already included on the Baccharis page but I want to flesh out a few of the mentions.

Uses

Piceol is used in the synthesis of several pharmaceutical drugs including octopamine, sotalol, bamethan, and dyclonine.[citation needed] We really need that citation because I looked up these drugs and wtf.

Anticonvulsants are also possible by Mannich reaction.

Metabolism

Diprenylated derivatives of piceol can be isolated from Ophryosporus macrodon (a genus of South American flowering plants in the tribe Eupatorieae).

4-Hydroxyacetophenone monooxygenase is an enzyme that transforms piceol into O-acetylhydroquinone. This enzyme is found in Pseudomonas fluorescens (and that definitely needs its own page).

See also

References

Chemical compound p-Hydroxyacetophenone found in:

Baccharis is a genus of perennials and shrubs in…

Herma

Theca

Xylotheque

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Piceol is used in the synthesis of several pharmaceutical drugs including octopamine, sotalol, bamethan, and dyclonine.^{[citation needed]} We really need that citation because I looked up these drugs and wtf.