Basic information
- CAS
5957-80-2- Standard SMILES
CC(C)c1cc2c(c(O)c1O)C13CCCC(C)(C)C1CC2OC3=O- InChIKey
XUSYGBPHQBWGAD-UHFFFAOYSA-N- Molecular formula
- C20H26O4
- Average molar mass
- 330.4 g/mol
- Monoisotopic mass
- 330.18310931
Overview
(1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one has been reported in Salvia officinalis, Salvia chionopeplica, and other organisms with data available.
Names & identifiers
- Preferred name
- (1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
- IUPAC
- 3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
- English name
- CARNOSOL
- Molecular formula
- C20H26O4
- Molecular weight
- 330.42
Names & synonyms
(1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-oneCarnosol [M+H]+MEGxp0_001119orb1221988SCHEMBL18290355XUSYGBPHQBWGAD-UHFFFAOYSA-NHMS3649B031,3,4,9,10,10aS-Hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4aR-(epoxymethano)phenanthren-12-oneNSC39143s9127EBC-627307SMP2_000248
Show more names
carnolCARNOSOLBCL6-IN-13D-α-AlanineCarnosol-RMCARNOSOL(RG)CARNOSOL USP/EP/BPCarnosol (Standard)Carnosol, 10 mM in DMSOCarnosol(P)(Request Quote)
NCGC00344316-023,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-oneSR-01000946633SR-01000946633-1(1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.0^{1,10.0^{2,7]hexadeca-2,4,6-trien-15-one1,3,4,9,10,10aS-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4aR-(epoxymethano)phenanthren-12-one (Musechem)3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
Properties
Computed structural properties
- XLogP
- 4.4
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 542
Physicochemical properties
- Melting point
- 240 · 240~242℃
- Boiling point
- 524.8 · 524.8±50.0 °C(Predicted)
- Density
- 1.26 · 1.26±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- 66 · DMSO:66.0(Max Conc. mg/mL);199.74(Max Conc. mM)
- form
- Solid
- pka
- 8.91 · 8.91±0.40(Predicted)
- color
- White
- biological source
- Rosemarinus officinalis L. leaves
- Major Application
- food and beverages
- InChI
- InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1
- InChIKey
- XUSYGBPHQBWGAD-PJSUUKDQSA-N
- SMILES
- C1(C)(C)[C@@]2([H])[C@]3(C(=O)O[C@@]([H])(C2)C2=C3C(O)=C(O)C(C(C)C)=C2)CCC1
- LogP
- 2.832 · 2.832 (est)
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
- wgk
- 3
- hs_code
- 29322090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Hazard Classifications
- Skin Sens. 1
- Precautionary statements
- P280-P302+P352
- Hazardous Substances Data
- 5957-80-2(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionCarnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen.
DescriptionCarnosol is a phenol that has been found in rosemary (R. officinalis) and has diverse biological activities. It decreases nitric oxide (NO) production in mouse peritoneal exudate macrophages when used at concentrations ranging from 6 to 25 μM. Carnosol scavenges peroxyl and hydroxyl radicals and inhibits lipid peroxidation in cell-free assays. It inhibits 5-lipoxygenase (5-LO; IC50 = 0.1 μM for the recombinant human enzyme) and the synthesis of leukotrienes in human polymorphonuclear leukocytes (PMNs; IC50 = 7 μM). In vivo, carnosol (200 mg/kg) reduces mammary DNA adduct formation and tumorigenesis in a rat model of DMBA-induced mammary tumorigenesis.
UsesCarnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen.
Upstream & downstream products
Downstream products
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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