spinochrome C | 3468-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: spinochrome C
• 英文别名: 3-acetyl-2,5,6,7,8-pentahydroxy-1,4-naphthoquinone；2-acetyl-3,5,6,7,8-pentahydroxy-[1,4]naphthoquinone；2-Acetyl-3,5,6,7,8-pentahydroxy-[1,4]naphthochinon；2-Acetyl-3,5,6,7,8-pentahydroxy-1,4-naphthochinon；2,6,7-Trihydroxy-3-acetylnaphthazarin
• CAS: 3468-83-5
• 化学式: C₁₂H₈O₈
• 分子量: 280.191
• InChiKey: ULXZDPXLOCDINN-UHFFFAOYSA-N

物化性质

• 沸点：
  775.6±60.0 °C(Predicted)
• 密度：
  1.994±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  20.0
• 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：
  152.36
• 氢给体数：
  5.0
• 氢受体数：
  8.0

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  cumyl peroxy radical 、 spinochrome C 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：

  3-acetyl-2,5,8-trihydroxy-6,7-dimethoxy-1,4-naphthoquinone 在 氢溴酸 作用下， 以40%的产率得到spinochrome C
  参考文献：
  名称：

  海胆色素 Spinochrome C 的简单合成

  摘要：

  3-Acetyl-2,5,6,7,8-pentahydroxy-1,4-naphthoquinone（3-acetyl-2,6,7-trihydroxynaphthazarine, spinochrome C, 1a）是一种海胆（Echinoidea 类）代谢物 [ 1]。除了来自该动物类别的其他经典醌型色素外，棘色素 C 还是一种有效的抗氧化剂 [2]。已知的合成棘色素 C 的方法通常需要几个步骤并且产率较低 [3]。我们发现，在含有 H2O 的 CCl4 中，Br2 对相对可用的棘色素 (2) [4] 的二甲醚进行溴化，形成了棘色素 C (3) 的二甲醚（产率 30%）（方案 1）。化合物 3 可能是在二溴化 4 的反应过程中形成的水​​解产物。用浓加热二醚 3。HBr (90°C) 得到旋光色素 C（1a，40%）及其脱酰产物旋光色素 D（2,6,7-三羟基萘扎林，1b，40%）。

  DOI：

  10.1007/s10600-016-1825-y

文献信息

• Spinochrome synthesis
  作者：I. Singh、R.E. Moore、C.W.J. Chang、R.T. Ogata、P.J. Scheuer

  DOI：10.1016/s0040-4020(01)98704-6

  日期：1968.1

  widely distributed structural pigments of the sea urchins (echinoids) one (spinochrome B) is a derivative of juglone, while four (spinochromes A, C, D, and E) are derivatives of naphthazarin. In addition to the two peri OH groups of naphthazarin these compounds bear one or more β-hydroxyls and/or an acetyl side chain. The synthesis of these four naphthazarin derivatives is described. The naphthalene skeleton

  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。
• 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。
• Kuhn; Wallenfels, Chemische Berichte, 1941, vol. 74, p. 1594,1598
  作者：Kuhn、Wallenfels

  DOI：——

  日期：——
• 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.
• [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.