ChemicalBook > CAS DataBase List > Costunolide

Costunolide

Product Name
Costunolide
CAS No.
553-21-9
Chemical Name
Costunolide
Synonyms
COSTUNDIDE;costunolid;Costunlide;(3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one;Costulide;NSC 106404;costunoide;CUSTUNOLIDE;COSTUNOLIDE;Cosinolactone
CBNumber
CB1455816
Molecular Formula
C15H20O2
Formula Weight
232.32
MOL File
553-21-9.mol
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Costunolide Property

Melting point:
106-107 °C
Boiling point:
385.4±42.0 °C(Predicted)
Density 
1.03±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: soluble10mg/mL (clear solution)
form 
powder
color 
white to beige
InChI
InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5+,11-9+/t13-,14+/m0/s1
InChIKey
HRYLQFBHBWLLLL-GRFSRWIASA-N
SMILES
O1C(=O)C(=C)[C@]2([H])CCC(C)=CCCC(C)=C[C@@]12[H] |t:10,15|
LogP
4.049 (est)
CAS DataBase Reference
553-21-9(CAS DataBase Reference)
NIST Chemistry Reference
Germacra-1(10),4,11(13)-trien-12-oic acid, 6«alpha»-hydroxy-, «gamma»-lactone, (e,e)-(553-21-9)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-24/25
WGK Germany 
3
HS Code 
29322090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0417
Product name
Costunolide
Purity
≥97% (HPLC)
Packaging
5mg
Price
$116
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0417
Product name
Costunolide
Purity
≥97% (HPLC)
Packaging
25mg
Price
$458
Updated
2024/03/01
TCI Chemical
Product number
C2921
Product name
Costunolide
Purity
>95.0%(HPLC)
Packaging
25mg
Price
$135
Updated
2024/03/01
TCI Chemical
Product number
C2921
Product name
Costunolide
Purity
>95.0%(HPLC)
Packaging
100mg
Price
$370
Updated
2024/03/01
Cayman Chemical
Product number
14743
Product name
Costunolide
Purity
≥98%
Packaging
1mg
Price
$29
Updated
2024/03/01
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Costunolide Chemical Properties,Usage,Production

Description

Costunolide is a germacranolide sesquiterpene lactone extracted from costus oil. With alantolactone and dehydrocostuslactone, it is a component of lactone mix used to elicit reactions in Compositae-sensitive patients. An erythema-multiform-like occupational contact dermatitis case occurred in a chemistry student after accidental exposure to costus oil (CJ Le Coz & JP Lepoittevin, unpublished results).

Chemical Properties

White crystalline powder, soluble in chloroform, derived from woodsy, Inula magnifica, Kerria japonica, Malachite.

Uses

Costunolide is the oil extracted from Saussurea lappa is used in perfumery and in the Orient for all kinds of diseases.

Uses

(+)-Costunolide is an inhibitor of osteoclast differentiation, acting as an anti-inflammatory and anti-oxidant agent. It is a sesquiterpene lactone which mediates apoptosis.

Definition

ChEBI: Costunolide is a germacranolide with anthelminthic, antiparasitic and antiviral activities. It has a role as an anthelminthic drug, an antiinfective agent, an antineoplastic agent, an antiparasitic agent, an antiviral drug and a metabolite. It is a germacranolide and a heterobicyclic compound.

General Description

Costunolide has anti-ulcer and antipyretic properties. It inhibits the cellular proliferation of melanin, human lamin-B by farnesyl-protein transferase (FPTase) and protein tyrosine phosphatase 1B (hPTP1B). Costunolide has strong larvicidal activity against A.albopictus. It inhibits the expression of inducible nitric oxide synthase and DNA-binding activity of nuclear factor kappa B subunit (NF-κB). It might function as a natural herbicide.

Biological Activity

Inhibitor of human telomerase activity (IC 50 = 65 μ M in MCF-7 breast cancer cells). Suppresses proliferation and induces apoptosis in a variety of human tumor cell lines. Selectively blocks endothelial cell proliferation induced by VEGF. Inhibits expression of iNOS and IL-1 β and disrupts NF- κ B activation. Displays anti-inflammatory, antifungal and antiviral properties.

Contact allergens

This germacranolide sesquiterpene lactone is extracted from costus oil. With alantolactone and dehydrocostunolide, it is a component of lactone mix used to elicit reactions in patients sensitive to Asteraceae-Compositae. An erythema-multiform-like occupational contact dermatitis case occurred in a chemical student after an accidental exposure to costus oil.

Biochem/physiol Actions

Costunolide is a sesquiterpene lactone originally isolated from plants widely used in many herbal medicines. It has a variety of effects. Costunolide is a potent inducer of apoptosis, a potent anti-cancer agent, has anti-inflammatory, anti-viral, anti-fungal, antimycobacterial activity and has been shown to inhibit telomerase activity.

Costunolide Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Costunolide manufacturers

Shanghai Standard Technology Co., Ltd.
Product
Costunolide 553-21-9
Price
US $0.00/mg
Min. Order
5mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2019-10-12
Shanghai Standard Technology Co., Ltd.
Product
Costunolide 553-21-9
Price
US $0.00/mg
Min. Order
5mg
Purity
Analytical Standard
Supply Ability
10 g
Release date
2019-10-12
NanJing Spring & Autumn Biological Engineering CO., LTD.
Product
Costundide 553-21-9 553-21-9
Price
US $25.00/mg
Min. Order
20mg
Purity
≥98%
Supply Ability
1000.00 kgs
Release date
2019-07-15

553-21-9, CostunolideRelated Search:


  • Costundide 553-21-9
  • (3AS,6E,10E,11AR)-3A,4,5,8,9,11A-HEXAHYDRO-6,10-DIMETHYL-3-METHYLENE-CYCLODECA[B]FURAN-2(3H)-ONE
  • COSTUNOLIDE
  • (e,e)-6-alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oicacidgamma-lactone
  • costunolid
  • germacra-1(10),4,11(13)-trien-12-oicacid,6-alpha-hydroxy-,gamma-lactone,(e,
  • Costunolide (NSC-106404)
  • Costunolide, 98%, from Saussurea costus (Falc.) Lipsch.
  • Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3- methylene-, [3aS-(3aR*,6E,10E,11aS*)]-
  • CUSTUNOLIDE
  • Cyclodeca[b]furan-2(3H)-one,3a,4,5,8,9,11a-
  • hexahydro-6,10-dimethyl-3-methylene-,(3aS,6E,10E,11aR)-
  • (3aS,6E,10E)-3aβ,4,5,8,9,11aβ-Hexahydro-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-one
  • (3aS,6E,10E)-3-Methylene-6,10-dimethyl-2,3,3aβ,4,5,8,9,11aα-octahydrocyclodeca[b]furan-2-one
  • Costulide
  • Costunlide
  • (3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[d]furan-2-one
  • COSTUNDIDE
  • NSC 106404
  • Costunolide, froM Auckiandialappa Decne.
  • (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3,3a,4,5,8,9-hexahydrocyclodeca[b]furan-2(11aH)-one
  • Costunolide, >=98%
  • Costunolide CRS
  • Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS,6E,10E,11aR)-
  • Costunolide,(S)
  • (3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
  • costunoide
  • Cosinolactone
  • Costus lactone|||NSC 106404|||Costunolid|||(+)-Costunolide
  • Costunolide(AS)
  • 553-21-9
  • Sesquiterpenoids
  • Inhibitors
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • chiral
  • Miscellaneous Natural Products