357995
香紫苏醇
98%
别名:
Labd-14-烯-8,13-二醇, (1R,2R,8aS)-十氢-1-(3-羟基-3-甲基-4-戊烯基)-2,5,5,8a-四甲基-2-萘酚
质量水平
方案
98%
旋光性
[α]25/D −13°, c = 4 in carbon tetrachloride
沸点
218-220 °C/19 mmHg (lit.)
mp
95-100 °C (lit.)
官能团
hydroxyl
SMILES字符串
CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@](C)(O)[C@@H]2CC[C@@](C)(O)C=C
InChI
1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1
InChI key
XVULBTBTFGYVRC-HHUCQEJWSA-N
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一般描述
香紫苏醇是具有半日花烷骨架的二萜化合物，主要用作香料工业中的原料。 它对人白血病细胞系表现出强效的细胞毒性和细胞抑制作用。
应用
香紫苏醇可以用作合成龙涎香化学制剂的原料，如龙涎醚、降龙涎香醚、甲基龙涎醚、ambracetal、ambraketal和epiambraketal。 它也可用于合成(+)-高良姜萜内酯、(-)-8-表-高良姜萜内酯和(+)-labdienedial。
储存分类代码
11 - Combustible Solids
WGK
WGK 2
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
Eyeshields, Gloves, type N95 (US)
Conversion of sclareol into (+)-galanolactone and (+)-labdienedial.
Jung M, et al.
Tetrahedron Letters, 38(16), 2871-2874 (1997)
Synthesis of ambergris fragrance chemicals from sclareol, involving palladium catalysed key steps.
Coste-Maniere IC, et al.
Tetrahedron Letters, 29(9), 1017-1020 (1988)
Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture.
Caniard A, et al.
BMC plant biology, 12(1), 119-119 (2012)
A short efficient synthesis of ambraketal (four steps) and epiambraketal (five steps) from Sclareol.
Martres P, et al.
Tetrahedron Letters, 35(1), 97-98 (1994)
Xiaolei Gao et al.
Organic letters, 8(10), 2123-2126 (2006-05-05)
[reaction: see text] A three-step route from sclareol oxide (6) to bromo ester 4 in 53% overall yield was achieved using the efficient oxidation of an allylic bromide to an enal with bis(2,4,6-trimethylpyridine)silver(I) hexafluorophosphate in DMSO. Stille coupling of bromo
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