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Cyclandelate

HCID 2893
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
456-59-7
Standard SMILES
CC1CC(OC(=O)C(O)c2ccccc2)CC(C)(C)C1
InChIKey
WZHCOOQXZCIUNC-UHFFFAOYSA-N
Molecular formula
C17H24O3
Average molar mass
276.376 g/mol
Monoisotopic mass
276.17254463

Names & identifiers

Preferred name
Cyclandelate
IUPAC
3,3,5-Trimethylcyclohexyl hydroxy(phenyl)acetate
English name
CYCLANDELATE
Molecular formula
C17H24O3
Molecular weight
276.37

Names & synonyms

3,3,5-TRIMETHYLCYCLOHEXYL MANDELATEbs572CydelNatilandeLBS 572CapilanAnaspatLejopanDilatan

Database identifiers

CAS
456-59-7
PubChem CID
2893
DTXSID
DTXSID4022862
ChEMBL
CHEMBL1480987
ChEBI
CHEBI:3988
UNII
4139O1OAY2
EC Number
207-271-6
Nikkaji
J2.048F

Properties

Physicochemical properties

Melting point
55 · 55.0-56.5°
Boiling point
14 · bp14 192-194°
Density
1.0535 · 1.0535 (rough estimate)
refractive index
1.549 · 1.5490 (estimate)
storage temp.
Sealed in dry,Room Temperature
Water Solubility
Insoluble in water
solubility
Chloroform (Slightly), Methanol (Slightly, Sonicated)
form
powder to crystal
pka
12.13 · 12.13±0.20(Predicted)
color
White to Almost white
Merck
14 · 14,2704
InChI
InChI=1S/C17H24O3/c1-12-9-14(11-17(2,3)10-12)20-16(19)15(18)13-7-5-4-6-8-13/h4-8,12,14-15,18H,9-11H2,1-3H3
InChIKey
WZHCOOQXZCIUNC-UHFFFAOYSA-N
SMILES
C1(CC(CC(C)(C)C1)C)OC(=O)C(O)C1C=CC=CC=1
FDA UNII
4139 O1OAY2 · 4139O1OAY2
ATC code
4 AX01 · C04AX01
EPA Substance Registry System
3 · Benzeneacetic acid, .alpha.-hydroxy-, 3,3,5-trimethylcyclohexyl ester (456-59-7)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
319 · H319
Precautionary statements
264 · P264-P280-P305+P351+P338-P337+P313P
RTECS
8200000 · OO8200000
TSCA
TSCA listed

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

tsca
TSCA listed
rtecs
OO8200000
hs_code
2918191350
Toxicity
LD50 oral in rat: 5gm/kg
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H319
Precautionary statements
P264-P280-P305+P351+P338-P337+P313P
Hazardous Substances Data
456-59-7(Hazardous Substances Data)

Chemistry & industry

Applications · 3 items

DescriptionAlmond (Amygdalus communis L) is a kind of nut from Xinjiang, China. Traditional Chinese medicine believes that almond can promote blood circulation to dispel blood stasis, lubricate bowels to relieve constipation, and relieve cough and asthma. The indications include amenorrhea, fever, wind arthralgia, malaria, blood stasis and pain, injuries, and blood stasis with constipation.

HistoryThe chemical synthesis of cyclandelate was first synthesized by Funcke et al. from Elan Corporation in Ireland using a-hydroxyphenylacetic acid and cis-3,3,5-cycloalkyl cyclohexanol. The raw material of mandelic acid was obtained by hydrolysis after benzaldehyde reacted to sodium cyanide. However, sodium cyanide is hypertoxic, and because of its unique structure of a-hydroxy acid, it is easy to decompose under the acid condition, which leads to more by-products and low yield. A series of improved methods have been developed, which can reduce the environmental pollution under the premise of ensuring the yield of Zn/HCOONH4/ C2H5OH system . The method was used to synthesize cyclandelate since then. However, this drug has not yet been approved by the Food and Drug Administration in the United States, Canada, and other countries because it easily causes white blood cell deficiency. It has been withdrawn from the market after drug approval in Japan, France, and other countries in the 1970s.

Usesvasodilator

Upstream & downstream products

Upstream raw materials

DL-Mandelic acid3,3,5-trimethylcyclohexyl 2-oxo-2-phenylacetate3,3,5-TrimethylcyclohexanolBenzoylformic acid

Suppliers100 total

国药集团化学试剂有限公司

Related reactions

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
HS Code
2918191350 · 2918191350
Hazardous Substances Data
456 · 456-59-7(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 5gm/kg
86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
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贵州迪大科技有限责任公司0851-8475-2296 18096062265 · [email protected]
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上海孚一生物科技有限公司+86 (21) 61124340
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上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
武汉鑫儒化工有限公司15927387915 15337108568
湖北辰心化工有限公司17362916295
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湖南瑞威尔生物科技有限公司18502762003
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Additional notes

DefinitionChEBI: The ester obtained by formal condensation of mandelic acid and 3,3,5-tricyclohexanol. It is a direct-acting smooth muscle relaxant used to dilate blood vessels.