18680-27-8 Usage
Description
(1S,2S,3R,5S)-(+)-2,3-Pinanediol is a bicyclic monoterpene diol, which is a white to light beige crystalline powder or found in crystal form. It is known for its ability to induce differentiation of certain types of cells, such as S91 melanoma and PC12 pheochromocytoma cells.
Uses
Used in Pharmaceutical Industry:
(1S,2S,3R,5S)-(+)-2,3-Pinanediol is used as a therapeutic agent for its potential role in inducing differentiation of specific cancer cells, which could provide treatment options for melanoma and pheochromocytoma.
Used in Cosmetics Industry:
In the cosmetics industry, (1S,2S,3R,5S)-(+)-2,3-Pinanediol is used for sunless tanning applications, offering an alternative to traditional sun exposure for achieving a tanned appearance.
Used in Chemical Synthesis:
(1S,2S,3R,5S)-(+)-Pinanediol serves as a chiral reagent in the synthesis of homochiral α-hydroxyketones, which are important in the production of various pharmaceuticals and chemicals. It is also used in the resolution of prolineboronate esters, which are relevant in the field of asymmetric synthesis.
Used in Fragrance Industry:
(1S,2S,3R,5S)-(+)-2,3-Pinanediol is utilized in the transformation of isopinocampheol and caryophyllene oxide, which are compounds used in the creation of fragrances and perfumes.
Check Digit Verification of cas no
The CAS Registry Mumber 18680-27-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,6,8 and 0 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 18680-27:
(7*1)+(6*8)+(5*6)+(4*8)+(3*0)+(2*2)+(1*7)=128
128 % 10 = 8
So 18680-27-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8+,10-/m0/s1
18680-27-8Relevant articles and documents
Synthesis of Thrombin Inhibitor DuP 714
Wityak, John,Earl, Richard A.,Abelman, Matthew M.,Bethel, Yvonne B.,Fisher, Barbara N.,et al.
, p. 3717 - 3722 (1995)
The asymmetric synthesis of thrombin inhibitor DuP 714 (1) is described.The route uses the Matteson boronic ester homologation to prepare the key intermediate, α-aminoboronic acid 4.New methodology was developed for the formamidination of boroornithine peptides and for pinanediol boronate ester cleavage.
Discovery of novel 20S proteasome inhibitors by rational topology-based scaffold hopping of bortezomib
Xu, Yulong,Yang, Xicheng,Chen, Yiyi,Chen, Hao,Sun, Huijiao,Li, Wei,Xie, Qiong,Yu, Linqian,Shao, Liming
supporting information, p. 2148 - 2152 (2018/05/25)
A series of structurally novel proteasome inhibitors 1–12 have been developed based rational topology-based scaffold hopping of bortezomib. Among these novel proteasome inhibitors, compound 10 represents an important advance due to the comparable proteasome-inhibitory activity (IC50 = 9.7 nM) to bortezomib (IC50 = 8.3 nM), the remarkably higher BEI and SEI values and the effectiveness in metabolic stability. Therefore, compound 10 provides an excellent lead suitable for further optimization.
A Modular Approach to the Asymmetric Synthesis of Cytisine
Struth, Felix R.,Hirschhaüser, Christoph
supporting information, p. 958 - 964 (2016/03/01)
The asymmetric synthesis of (+)-and (-)-cytisine starts with Matteson homologations for the construction of a chiral C3-building block. Conversion of the C3-building block into a dihydropyridone is achieved by straightforward functional group interconversions and ring closing metathesis. After bromination, this central building block was diastereospecifically converted into cytisine in five steps.
