4-methyl-5-n-pentylbenzene-1,3-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-methyl-5-n-pentylbenzene-1,3-diol
• 英文别名: 4-methyl-5-pentylbenzene-1,3-diol；MPBD
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: CUXFFBBWEJOYAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2,4-dihydroxy-6-pentylbenzaldehyde	855875-40-0	C12H16O3	208.257
  3,5-二羟基戊苯	Olivetol	500-66-3	C11H16O2	180.247

反应信息

• 作为反应物：
  描述：

  4-methyl-5-n-pentylbenzene-1,3-diol 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 氘代甲醇 作用下， 以 水 、 丙酮 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  Alkylbenzoquinone Involved in Development of Cellular Slime Molds

  摘要：

  The structure of the prespore-cell-promoting factor from Dictyostelium discoideum was determined to be 2-hydroxy-5-methyl-6-pentylbenzoquinone. The synthetic compound has prespore-cell-promoting activity similar to the natural one, with half-maximal induction at a concentration as low as 40 pM. It was also found that the factor induces aggregation in an aggregation-deficient mutant of a related species, Polysphodilium violaceum. Both these activities are sensitive to positional isomerism with the 6-methyl-5-pentyl isomer showing no detectable activity.

  DOI：

  10.1021/ol5014119
• 作为产物：
  描述：

  3,5-二羟基戊苯 在 红铝 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 4-methyl-5-n-pentylbenzene-1,3-diol
  参考文献：
  名称：

  [EN] CANNABINOID DERIVATIVES AND THEIR USE THE TREATMENT OF INFLAMMATION AND/OR PAIN AND/OR OBESITY
  [FR] DÉRIVÉS CANNABINOÏDES ET LEUR UTILISATION DANS LE TRAITEMENT DE L'INFLAMMATION ET/OU DE LA DOULEUR ET/OU DE L'OBÉSITÉ

  摘要：

  The invention provides cannabinoid derivatives, methods of their preparation, compositions comprising them and uses thereof in the treatment of inflammation and/or pain and/or obesity.

  公开号：

  WO2022113071A2

文献信息

• Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol (MPBD), produced by Dictyostelium discoideum
  作者：Chihiro Murata、Tetsuhiro Ogura、Shuhei Narita、Anna P. Kondo、Natsumi Iwasaki、Tamao Saito、Toyonobu Usuki

  DOI：10.1016/j.bmcl.2016.01.067

  日期：2016.3

  4-Methyl-5-pentylbenzene-1,3-diol (MPBD) is a secondary metabolite of SteelyA polyketide synthase, which controls cell aggregation and spore maturation of Dictyostelium discoideum. In this study, chemical synthesis of MPBD and its derivatives was achieved. Structure–activity relationship (SAR) studies for antimicrobial activities against Escherichia coli and Bacillus subtilis were also conducted.

  4-甲基-5-戊-1,3-二醇（MPBD）是SteelyA聚酮化合物合酶的次级代谢产物，其中的控制细胞聚集和孢子成熟粘菌。在这项研究中，实现了MPBD及其衍生物的化学合成。还进行了针对大肠杆菌和枯草芽孢杆菌的抗菌活性的结构-活性关系（SAR）研究。
• Method and cell line for production of polyketides in yeast
  申请人：Hyasynth Biologicals Inc.

  公开号：US10975395B2

  公开（公告）日：2021-04-13

  A method and cell line for producing polyketides in yeast. The method applies, and the cell line includes, a yeast cell transformed with a polyketide synthase coding sequence. The polyketide synthase enzyme catalyzes synthesis of olivetol or methyl-olivetol, and may include Dictyostelium discoideum polyketide synthase (“DiPKS”). Wild type DiPKS produces methyl-olivetol only. DiPKS may be modified to produce olivetol only or a mixture of both olivetol and methyl-olivetol. The yeast cell may be modified to include a phosphopantethienyl transferase for increased activity of DiPKS. The yeast cell may be modified to mitigate mitochondrial acetaldehyde catabolism for increasing malonyl-CoA available for synthesizing olivetol or methyl-olivetol.

  一种在酵母中生产多酮苷的方法和细胞系。该方法适用于用多酮合成酶编码序列转化的酵母细胞，细胞系包括酵母细胞。多酮合成酶催化橄榄醇或甲基-橄榄醇的合成，可包括盘基竹荪多酮合成酶（"DiPKS"）。野生型 DiPKS 只产生甲基-橄榄醇。可对 DiPKS 进行改造，使其只产生橄榄醇或橄榄醇和甲基-橄榄醇的混合物。可对酵母细胞进行改造，使其包括磷酸泛硫氨基转移酶，以提高 DiPKS 的活性。可对酵母细胞进行改造，以减轻线粒体乙醛分解，从而增加丙二酰-CoA 可用于合成橄榄醇或甲基橄榄醇。
• Method and cell line for production of phytocannabinoids and phytocannabinoid analogues in yeast
  申请人：Hyasynth Biologicals Inc.

  公开号：US11312979B2

  公开（公告）日：2022-04-26

  A method and cell line for producing phytocannabinoids and phytocannabinoid analogues in yeast. The method applies, and the cell line includes, a yeast cell transformed with a polyketide synthase CDS and a cytosolic prenyltransferase CDS. The polyketide synthase enzyme catalyzes synthesis of olivetol or methyl-olivetol, and may include Cannabis sativa olivetolic acid synthase or Dictyostelium discoideum polyketide synthase (“DiPKS”). The yeast cell may be modified to include a phosphopantethienyl transferase for increased activity of DiPKS. The yeast cell may be modified to mitigate mitochondrial acetaldehyde catabolism for increasing malonyl-CoA available for synthesizing olivetol or methyl-olivetol. The prenyltransferase enzyme catalyzes synthesis of cannabigerol or a cannabigerol analogue, and may include an αββα cytosolic prenyltransferase enzyme from Streptomyces sp CL190. The yeast cell may be modified to mitigate depletion of geranyl pyrophosphate for increasing available geranyl pyrophosphate for prenylation.

  一种在酵母中生产植物大麻素和植物大麻素类似物的方法和细胞系。该方法应用的细胞系包括转化了多酮合成酶 CDS 和细胞质前酰转移酶 CDS 的酵母细胞。多酮合成酶催化橄榄醇或甲基-橄榄醇的合成，可包括大麻橄榄醇酸合成酶或盘状竹荪多酮合成酶（"DiPKS"）。可以对酵母细胞进行改造，使其包括磷酸泛硫氨基转移酶，以提高 DiPKS 的活性。可对酵母细胞进行改造，以减轻线粒体乙醛分解，从而增加丙二酰-CoA 可用于合成橄榄醇或甲基-橄榄醇。前基转移酶催化大麻酚或大麻酚类似物的合成，可包括来自链霉菌 CL190 的 αββα 细胞质前基转移酶。可对酵母细胞进行改造，以减少焦磷酸香叶酯的消耗，增加可用于预炔化的焦磷酸香叶酯。
• METHODS AND CELLS FOR PRODUCTION OF PHYTOCANNABINOIDS AND PHYTOCANNABINOID PRECURSORS
  申请人：Hyasynth Biologicals Inc.

  公开号：EP3973061A1

  公开（公告）日：2022-03-30
• REDUCTION OF BETA-AMYLOID LEVELS BY TREATMENT WITH THE SMALL MOLECULE DIFFERENTIATION-INDUCING FACTOR
  申请人：Myre Michael

  公开号：US20100311726A1

  公开（公告）日：2010-12-09

  The present invention relates to novel uses for a family of small molecules, Differentiation-Inducing Factors (DIFs). It has been discovered that DIFs surprisingly can alter the metabolic processing of amyloid precursor protein (APP) and in turn reduce the level of secreted Aβ. The metabolic processing of other γ-secretase substrates normally present in cells (Notch and APLP1) is not affected when treated with DIF. The invention provides methods for reducing Aβ production in mammalian cells that express APP by administering DIF-I, DIF-2, DIF-3, a functionally equivalent analog and or any combination thereof. The invention also provides methods for treating and/or preventing Alzheimer's disease by preferentially reducing Aβ production.