(E)-4-(3,7-Dimethyl-2,6-octadienyl)-5-pentyl-1,3-benzenediol | 55854-24-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-4-(3,7-Dimethyl-2,6-octadienyl)-5-pentyl-1,3-benzenediol
• 英文别名: 4-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentylbenzene-1,3-diol
• CAS: 55854-24-5
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: JFJAMLJGMDJCRJ-SFQUDFHCSA-N

物化性质

• 沸点：
  464.6±45.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  香叶基焦磷酸铵盐 、 3,5-二羟基戊苯 在 Tris-HCl buffer 、 magnesium chloride 作用下， 生成 (E)-4-(3,7-Dimethyl-2,6-octadienyl)-5-pentyl-1,3-benzenediol 、 大麻萜酚
  参考文献：
  名称：

  Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities

  摘要：

  NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3( 2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.052

文献信息

• SYNTHESIS OF CANNABIGEROL
  申请人：Canopy Holdings, LLC

  公开号：US20200115306A1

  公开（公告）日：2020-04-16

  Multiple methods of synthesizing cannabigerol are presented. Combining olivetol with geraniol derivatives are provided. Cross-coupling methods of combing functionalized resorcinols are provided. Useful intermediates are formed during such cross-coupling steps.

  提供了多种合成大麻酚的方法。提供了将奥利维托尔与香叶醇衍生物结合的方法。提供了结合功能化间苯二酚的交叉偶联方法。在这种交叉偶联步骤中形成了有用的中间体。
• [EN] SYNTHESIS AND PURIFICATION OF CANNABIGEROL AND ITS APPLICATION<br/>[FR] SYNTHÈSE ET PURIFICATION DE CANNABIGÉROL ET SON UTILISATION
  申请人：SYMRISE AG

  公开号：WO2020249184A1

  公开（公告）日：2020-12-17

  The present invention relates to a method for producing cannabigerol and purifying it from a reaction mixture. The present invention also relates to the cosmetic use of cannabigerol for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, in particular for reducing pigmentation of the skin, preferably for the improvement of the appearance of the skin in case of hyperpigmentation, lentigo or vitiligo. Furthermore, the present invention relates to cannabigerol for use in a therapeutic method for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, preferably for use in a therapeutic method for the treatment and/or prevention of malign skin disorders, in particular skin cancer.

  本发明涉及一种从反应混合物中生产大麻生酚并对其进行纯化的方法。本发明还涉及大麻生酚在化妆品中的应用，用于抑制酪氨酸酶活性和/或减少皮肤中黑色素的产生，特别是用于减少皮肤的色素沉着，优选用于改善皮肤在色素沉着过多、雀斑或白癜风等情况下的外观。此外，本发明涉及大麻生酚用于治疗方法，用于抑制皮肤中酪氨酸酶活性和/或减少黑色素的产生，特别是用于治疗和/或预防恶性皮肤疾病，特别是皮肤癌的治疗方法。
• Synthesis of cannabigerol
  申请人：Treehouse Biotech, Inc.

  公开号：US11040932B2

  公开（公告）日：2021-06-22

  Multiple methods of synthesizing cannabigerol are presented. Combining olivetol with geraniol derivatives are provided. Cross-coupling methods of combing functionalized resorcinols are provided. Useful intermediates are formed during such cross-coupling steps.

  介绍了合成大麻酚的多种方法。提供了将橄榄醇与香叶醇衍生物相结合的方法。提供了结合官能化间苯二酚的交叉偶联方法。在此类交叉偶联步骤中会形成有用的中间体。
• Novel aromatic prenyltransferases, nucleic acids encoding same and uses therefor
  申请人：Kuzuyama Tomohisa

  公开号：US20060183211A1

  公开（公告）日：2006-08-17

  In accordance with the present invention, a novel aromatic prenyltransferase, Orf2 from Streptomyces sp. strain CL190, involved in naphterpin biosynthesis has been identified and the structure thereof elucidated. This prenyltransferase catalyzes the formation of a C—C bond between a prenyl group and a compound containing an aromatic nucleus, and also displays C—O bond formation activity. Numerous crystallographic structures of the prenyltransferase have been solved and refined, e.g., (1) prenyltransferase complexed with a buffer molecule (TAPS), (2) prenyltransferase as a binary complex with geranyl diphosphate (GPP) and Mg 2+ , and prenyltransferase as ternary complexes with a non-hydrolyzable substrate analogue, geranyl S-thiolodiphosphate (GSPP) and either (3) 1,6-dihydroxynaphthalene (1,6-DHN), or (4) flaviolin (i.e., 2,5,7-trihydroxy-1,4-naphthoquinone, which is the oxidized product of 1,3,6,8-tetrahydroxynaphthalene (THN)). These structures have been solved and refined to 1.5 Å, 2.25 Å, 1.95 Å and 2.02 Å, respectively. This first structure of an aromatic prenyltransferase displays an unexpected and non-canonical (β/α)-barrel architecture. The complexes with both aromatic substrates and prenyl containing substrates and analogs delineate the active site and are consistent with a proposed electrophilic mechanism of prenyl group transfer. These structures also provide a mechanistic basis for understanding prenyl chain length determination and aromatic co-substrate recognition in this structurally unique family of aromatic prenyltransferases. This structural information is useful for predicting the aromatic prenyltransferase activity of proteins.

  根据本发明，一种新型芳香族前基转移酶 Orf2 来自于 链霉菌 菌株 CL190 中发现的一种参与萘素生物合成的新型芳香族前基转移酶 Orf2，并阐明了其结构。这种炔基转移酶催化炔基与含有芳香核的化合物之间形成 C-C 键，同时还具有形成 C-O 键的活性。前炔基转移酶的许多晶体结构已得到解决和完善，例如：（1）前炔基转移酶与缓冲分子（TAPS）的复合物；（2）前炔基转移酶与二磷酸香叶酯（GPP）和 Mg 2+ 和 (3) 1,6-二羟基萘（1,6-DHN）或 (4) 黄素（即 2,5,7-三羟基-1,4-萘醌，它是 1,3,6,8-四羟基萘（THN）的氧化产物）的三元复合物。这些结构已分别求解并精炼至 1.5 Å、2.25 Å、1.95 Å 和 2.02 Å。这是首个芳香族预烯基转移酶的结构，显示出一种意想不到的非经典（β/α）桶状结构。与芳香底物和含预烯醇底物及类似物的复合物划定了活性位点，并与所提出的预烯醇基团转移的亲电机制相一致。这些结构还为了解这一结构独特的芳香族前酰基转移酶家族的前酰基链长决定和芳香族共底物识别提供了机理基础。这些结构信息有助于预测蛋白质的芳香族前基转移酶活性。
• NOVEL AROMATIC PRENYLTRANSFERASES, NUCLEIC ACIDS ENCODING SAME AND USES THEREFOR
  申请人：Kuzuyama Tomohisa

  公开号：US20080274478A1

  公开（公告）日：2008-11-06

  In accordance with the present invention, a novel aromatic prenyltransferase, Orf2 from Streptomyces sp. strain CL190, involved in naphterpin biosynthesis has been identified and the structure thereof elucidated. This prenyltransferase catalyzes the formation of a C—C bond between a prenyl group and a compound containing an aromatic nucleus, and also displays C—O bond formation activity. Numerous crystallographic structures of the prenyltransferase have been solved and refined, e.g., (1) prenyltransferase complexed with a buffer molecule (TAPS), (2) prenyltransferase as a binary complex with geranyl diphosphate (GPP) and Mg 2+ , and prenyltransferase as ternary complexes with a non-hydrolyzable substrate analogue, geranyl S-thiolodiphosphate (GSPP) and either (3) 1,6-dihydroxynaphthalene (1,6-DHN), or (4) flaviolin (i.e., 2,5,7-trihydroxy-1,4-naphthoquinone, which is the oxidized product of 1,3,6,8-tetrahydroxynaphthalene (THN)). These structures have been solved and refined to 1.5 Å, 2.25 Å, 1.95 Å and 2.02 Å, respectively. This first structure of an aromatic prenyltransferase displays an unexpected and non-canonical (β/α)-barrel architecture. The complexes with both aromatic substrates and prenyl containing substrates and analogs delineate the active site and are consistent with a proposed electrophilic mechanism of prenyl group transfer. These structures also provide a mechanistic basis for understanding prenyl chain length determination and aromatic co-substrate recognition in this structurally unique family of aromatic prenyltransferases. This structural information is useful for predicting the aromatic prenyltransferase activity of proteins.