6-acetyl-4,5,7,8-tetrahydroxynaphthalene-1,2-dione | 3718-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-acetyl-4,5,7,8-tetrahydroxynaphthalene-1,2-dione
• 英文别名: 2-acetyl-3,5,6,8-tetrahydroxy-1,4-naphthoquinone (Spinochrome A)；3-acetyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone；spinochrome A；2-acetyl-3,5,6,8-tetrahydroxy-[1,4]naphthoquinone；2-Acetyl-3,5,6,8-tetrahydroxy-[1,4]naphthochinon；2,5,7,8-tetrahydroxy-3-acetyl-1,4-naphthoquinone；2,7-Dihydroxy-3-acetylnaphthazarin (Spinochrom A)
• CAS: 3718-80-7
• 化学式: C₁₂H₈O₇
• 分子量: 264.191
• InChiKey: UBUDVMJJWVUMCC-UHFFFAOYSA-N

物化性质

• 沸点：
  589.6±50.0 °C(Predicted)
• 密度：
  1.859±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  132.13
• 氢给体数：
  4.0
• 氢受体数：
  7.0

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  cumyl peroxy radical 、 6-acetyl-4,5,7,8-tetrahydroxynaphthalene-1,2-dione 生成 过氧化氢异丙苯
  参考文献：
  名称：

  Polyhydroxynaphthoquinones ? a new class of natural antioxidants

  摘要：

  DOI：

  10.1007/bf00950127
• 作为产物：
  描述：

  2,7-Diacetyl-3,6-dihydroxy-naphthazarin 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 6-acetyl-4,5,7,8-tetrahydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  旋色素的合成

  摘要：

  在海胆的五种广泛分布的结构性颜料（类神经碱）中，一种（螺闪体色素B）是朱古龙的衍生物，而四种（螺闪体色素A，C，D和E）是萘甲萘林的衍生物。除了这两个围萘他沙林的OH基团带有一个或多个β-羟基和/或乙酰基侧链。描述了这四种萘他林衍生物的合成。萘骨架是通过将1,2-二羟基-3,4-二甲氧基苯与氯-或二氯马来酸酐在铝-氯化钠熔体中缩合而构建的。通过用甲醇盐离子的亲核取代氯或通过Thiele方法引入了更多的氧官能团。通过制备无色乙酸酯并将其用乙酸酐-三氟化硼处理，将乙酰基侧链连接至聚羟基萘醌。在加工过程中水解和氧化后，萘扎林体系得以再生。

  DOI：

  10.1016/s0040-4020(01)98704-6

文献信息

• Polycyclic hydroxyquinones—VIII
  作者：Francisco Farin˜a、Roberto Martinez-Utrilla、M. Carmen Paredes

  DOI：10.1016/0040-4020(82)80244-5

  日期：1982.1

  Several synthetic routes to mono- and dihydroxynaphthazarins bearing an acetyl side-chain have been explored. Methoxynaphthazarin1 has always been the starting material. Acylation is brought aboutvia a photo-Fries rearrangement of various adequately substituted acetoxynaphthalenes prepared in several steps from1. Further steps including oxidative demethylation, hydrolysis and ether cleavage reactions

  已探索了几种带有乙酰基侧链的单和二羟基萘达那林的合成途径。甲氧基萘他林1一直是起始原料。通过从1开始的多个步骤制备的各种适当取代的乙酰氧基萘的光-弗里斯重排，实现酰化作用。进一步的步骤，包括氧化脱甲基，水解和醚裂解反应，产生了所需的单和二羟基取代的乙酰萘。描述了新合成的Spinochrome A 24（一种代表这种萘达那林衍生物的天然色素）。
• Method for producing a sea urchin extract enriched with 1,4-polyhydroxylated naphthoquinones with antimicrobial and antioxidant activity
  申请人：Universidad Técnica Federico Santa María

  公开号：US11007155B2

  公开（公告）日：2021-05-18

  The invention refers to a method for obtaining polyhydroxy 1,4-naphthoquinones from live sea urchins, comprising the following steps: a) injecting a KCl saline solution into the perivisceral coeloma of female sea urchins to induce spawning; b) collecting the eggs, and grinding them into a fine powder; c) mixing said fine powder with an alcoholic solvent; d) separating the alcohol supernatant comprising the polyhydroxy 1,4-naphthoquinones in solution. Where the polyhydroxy 1,4-naphthoquinones are selected from: echinochrome A (6-ethyl-2,3,5,7,8-pentahydroxy-1,4-naphthoquinone), spinochrome A (2-acetyl-3,5,6,8-tetrahydroxy-1,4-naphthoquinone), spinochrome B (2,3,5,7-tetrahydroxy-1,4-naphthoquinone), spinochrome C (2-acetyl-3,5,6,7,8-pentahydroxy-1,4-naphthoquinone), spinochrome D (2,3,5,6,8-pentahydroxy-1,4-naphthoquinone), spinochrome E (hexahydroxy-1,4-naphthoquinone) or mixtures thereof.

  本发明涉及一种从活海胆中获得多羟基 1,4-萘醌的方法，包括以下步骤： a) 将氯化钾盐溶液注射到雌性海胆的脐周海绵体中，以诱导产卵； b) 收集卵，并将其研磨成细粉 c) 将上述粉末与酒精溶剂混合； d) 分离含有多羟基 1,4-萘醌溶液的酒精上清液。 其中多羟基 1，4-萘醌选自echinochrome A (6-ethyl-2,3,5,7,8-pentahydroxy-1,4-naphthoquinone), spinochrome A (2-acetyl-3,5,6,8-tetrahydroxy-1,4-naphthoquinone), spinochrome B (2,3,5,7-tetrahydroxy-1,4-naphthoquinone)、或它们的混合物。
• COMPOSITION, USE THEREOF, AND METHODS OF MANUFACTURING
  申请人：FertileSea LLC

  公开号：US20160082050A1

  公开（公告）日：2016-03-24

  A composition that includes at least two of: echinochrome A (2-ethyl-3,5,6,7,8-pentahydroxy-1,4-naphthoquinone); spinochrome A (2-acetyl-3,5,6,8-tetrahydroxy-1,4-naphthalenedione); spinochrome B (2,3,5,7-tetrahydroxy-1,4-naphthalenedione); spinochrome C (2-acetyl-3,5,6,7,8-pentahydroxy-1,4-naphthalenedione); spinochrome D (2,3,5,6,8-Pentahydroxy-1,4-naphthalenedione); and spinochrome E (hexahydroxy-1,4-naphthalenedione). The composition can include one or more additional active ingredients (e.g., vitamin, tretinoin (alltrans retinoic acid or ATRA), a glycosaminoglycan (GAG), dermal filler, Botulinum toxin, etc.) and/or one or more inactive ingredients (e.g., solvent, carrier, gelling agent, coloring agent, etc.). The composition can be in a dry, solid form (e.g., powder), or in a liquid form. Additionally, each of the above components above can independently be present in the composition in either the naturally derived form, or in a synthetically prepared form.
• US4888026A
  申请人：——

  公开号：US4888026A

  公开（公告）日：1989-12-19
• [EN] METHOD FOR PRODUCING A SEA URCHIN EXTRACT ENRICHED WITH 1,4-POLYHYDROXYLATED NAPHTHOQUINONES WITH ANTIMICROBIAL AND ANTIOXIDANT ACTIVITY<br/>[ES] UN MÉTODO PARA PRODUCIR UN EXTRACTO DE ERIZOS MARINOS ENRIQUECIDO EN 1,4-NAFTOQUINONAS POLIHIDROXILADAS CON ACTIVIDADES ANTIMICROBIANAS Y ANTIOXIDANTES<br/>[FR] MÉTHODE DE PRODUCTION D'UN EXTRAIT D'OURSINS DE MER ENRICHIS EN 1,4-NAPHTHOQUINONES POLYHYDROXYLÉES AYANT DES ACTIVITÉS ANTIMICROBIENNES ET ANTIOXYDANTES
  申请人：UNIV TECNICA FEDERICO SANTA MARIA UTFSM

  公开号：WO2018085955A1

  公开（公告）日：2018-05-17

  La invención se refiere a un método para obtener 1,4-naftoquinonas polihidroxiladas desde erizos de mar vivos, que comprende las siguientes etapas: a) inyectar una solución salina de KCl en el celoma perivisceral de erizos de mar hembra para inducir el desove; b) recolectar las ovas, y molerlas hasta obtener un polvo fino; c) mezclar dicho polvo fino con un solvente alcohólico; d) separar el sobrenadante alcohólico que comprende las 1,4-naftoquinonas polihidroxiladas en solución. Donde las 1,4-naftoquinonas polihidroxiladas se escogen entre: equinocromo A (6-etil- 2,3,5,7,8-pentahidroxi-1,4-naftoquinona), espinocromo A (2-acetil-3,5,6,8-tetrahidroxi-1,4- naftoquinona), espinocromo B (2,3,5,7-tetrahidroxi-1,4-naftoquinona), espinocromo C (2- acetil-3,5,6,7,8- pentahidroxi-1,4-naftoquinona), espinocromo D (2,3,5,6,8-pentahidroxi- 1,4-naftoquinona), espinocromo E (hexahidroxi-1,4-naftoquinona) o sus mezclas.